dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a75e54f6a7504dcd907a03e3ff22457e | CC(=S)OCCl.Cn1ccnc1>>CC(=S)OC[n+]1ccn(C)c1.[Cl-] | CN1C=NC=C1.ClCOC(C)=S>>[Cl-].C(C)(=S)OC[N+]1=CN(C=C1)C | [CH3:1][C:2](=[S:3])[O:4][CH2:5][Cl:12].[n:6]1[cH:7][cH:8][n:9]([CH3:10])[cH:11]1>>[CH3:1][C:2](=[S:3])[O:4][CH2:5][n+:6]1[cH:7][cH:8][n:9]([CH3:10])[cH:11]1.[Cl-:12] | CC(=S)OCCl.Cn1ccnc1 | CC(=S)OC[n+]1ccn(C)c1.[Cl-] | null | null | null | Functional Group Interconversion | OtherReaction | f75f0e838a29c549290e6181c709c5384561f85dfac9d38699be07b677e32d50 | 42c71821dc42e0c1902cec868cf7d0abd0a4511b0313126f4c5eb9aac58d5cad | c1c[nH+]c[nH]1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[n;H0;D2;+0:4]:[c:5]:[c:6]:1.[C;D1;H3:7]-[C:8](=[S;D1;H0:9])-[#8:10]-[CH2;D2;+0:11]-[Cl;H0;D1;+0:12]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[n+;H0;D3:4](-[CH2;D2;+0:11]-[#8:10]-[C:8](-[C;D1;H3:7])=[S;D1;H0:9]):[c:5]:[c:6]:1.[Cl-;H0;D0:12] | null | [] | null | null | 10 | MINUTE | To 0.7 g (8.52 millimoles) of 1-methylimidazole was added slowly and with cooling, 1.5 g of (16.2 millimoles) chloromethylthioacetate. The solution solidified in 10 minutes and was left stoppered at room temperature overnight.
Conditions: See reaction.notes.procedure_details.
Workup: with cooling; was left; stoppered a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[n+]cn1 | c1c[n+]cn1 | null | null | null | 0.166667 | CC(=S)OCCl.Cn1ccnc1>>CC(=S)OC[n+]1ccn(C)c1.[Cl-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a9feead895f943e08dea8241895071cb | FC(F)(F)C(F)(F)C(F)(F)I.O=C(CCl)CCl.c1nc[nH]n1>>FC(F)(F)C(F)(F)C(F)(F)C1(Cn2cncn2)CO1 | N1N=CN=C1.C([O-])([O-])=O.[K+].[K+].ClCC(=O)CCl.[Cl-].[NH4+].C1(=CC=CC=C1)[Mg]Br.FC(C(F)(F)I)(C(F)(F)F)F>>FC(C(C1(OC1)CN1N=CN=C1)(F)F)(C(F)(F)F)F | I[C:8]([C:5]([C:2]([F:1])([F:3])[F:4])([F:6])[F:7])([F:9])[F:10].Cl[CH2:12][C:11]([CH2:18]Cl)=[O:19].[nH:13]1[cH:14][n:15][cH:16][n:17]1>>[F:1][C:2]([F:3])([F:4])[C:5]([F:6])([F:7])[C:8]([F:9])([F:10])[C:11]1([CH2:12][n:13]2[cH:14][n:15][cH:16][n:17]2)[CH2:18][O:19]1 | FC(F)(F)C(F)(F)C(F)(F)I.O=C(CCl)CCl.c1nc[nH]n1 | FC(F)(F)C(F)(F)C(F)(F)C1(Cn2cncn2)CO1 | null | null | CN(C=O)C.[Cl-].[Na+].O.O.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 5987faaf33ecde06088464172ca0b8907c36c6835b86556126be864a0e21a050 | 9463313198c4cf1e31239253ca680f9356f76442f90ead176638713b939bb0f8 | c1ncn(CC2CO2)n1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[CH2;D2;+0:4]-Cl.I-[C;H0;D4;+0:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[C:11](-[F;D1;H0:12])(-[F;D1;H0:13])-[F;D1;H0:14].[#7;a:15]1:[c:16]:[nH;D2;+0:17]:[#7;a:18]:[c:19]:1>>[F;D1;H0:6]-[C;H0;D4;+0:5](-[F;D1;H0:7])(-[C:8](-[F;D1;H0:9])(-[F;D1;H0:... | 2.1 | [{"value": 2.1, "product": "FC(C(C1(OC1)CN1N=CN=C1)(F)F)(C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of heptafluoropropyl iodide (14.58 g, 49.2 m.mole) in diethylether (65 ml) was stirred and cooled to -70°. A solution of phenylmagnesium bromide in diethylether (15.75 ml of a 3 molar solution; 47.25 m.mole) was then added dropwise at such a rate that the temperature of the reaction mixture did not exceed -6... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Primary halide.Primary halide.Ketone | Tertiary halide.Tertiary halide.Ether | c1nc[nH]n1 | c1nc[nH]n1.C1CO1 | c1nc[nH]n1.C1CO1 | HCl.I- | CN(C=O)C.[Cl-].[Na+].O.O.C(C)OCC | null | 0.25 | FC(F)(F)C(F)(F)C(F)(F)I.O=C(CCl)CCl.c1nc[nH]n1>CN(C=O)C.[Cl-].[Na+].O.O.C(C)OCC>FC(F)(F)C(F)(F)C(F)(F)C1(Cn2cncn2)CO1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-654d2a1fc7d54165a1a2363bf543e3e1 | CC(S(C)(=O)=O)S(=O)(=O)[O-].ClP(Cl)(Cl)(Cl)Cl>>CC(S(C)(=O)=O)S(=O)(=O)Cl | Cl.CS(=O)(=O)C(C)S(=O)(=O)[O-].[Na+].CS(=O)(=O)C(C)S(=O)(=O)[O-].[Na+].P(Cl)(Cl)(Cl)(Cl)Cl>>CS(=O)(=O)C(C)S(=O)(=O)Cl | [O-][S:7]([CH:2]([CH3:1])[S:3]([CH3:4])(=[O:5])=[O:6])(=[O:8])=[O:9].ClP(Cl)(Cl)(Cl)[Cl:10]>>[CH3:1][CH:2]([S:3]([CH3:4])(=[O:5])=[O:6])[S:7](=[O:8])(=[O:9])[Cl:10] | CC(S(C)(=O)=O)S(=O)(=O)[O-].ClP(Cl)(Cl)(Cl)Cl | CC(S(C)(=O)=O)S(=O)(=O)Cl | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | null | Cl-P(-Cl)(-Cl)(-Cl)-[Cl;H0;D1;+0:1].[#16:2]-[C:3](-[C;D1;H3:4])-[S;H0;D4;+0:5](-[O-])(=[O;D1;H0:6])=[O;D1;H0:7]>>[#16:2]-[C:3](-[C;D1;H3:4])-[S;H0;D4;+0:5](-[Cl;H0;D1;+0:1])(=[O;D1;H0:6])=[O;D1;H0:7] | null | [] | null | null | 20 | MINUTE | A mixture of 5 g of sodium 1-(methylsulfonyl)ethanesulfonate (Formula II, X=R=CH3, Y=Na) and 5.34 g of phosphorus pentachloride was stirred under an inert atmosphere at room temperature. After about 20 minutes, the evolution of hydrogen chloride and the generation of heat were observed, and shortly thereafter the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | null | Other | ClCCl | null | 0.333333 | CC(S(C)(=O)=O)S(=O)(=O)[O-].ClP(Cl)(Cl)(Cl)Cl>ClCCl>CC(S(C)(=O)=O)S(=O)(=O)Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e42584a889aa47489b41adbbc5fd7a0b | CCN(CC)CC.CS(=O)(=O)Cl.OCCCl>>CS(=O)(=O)CS(=O)(=O)OCCCl | C(C)N(CC)CC.ClCCO.CS(=O)(=O)Cl>>CS(=O)(=O)CS(=O)(=O)OCCCl | CCN(CC)C[CH3:1].Cl[S:2](=[O:3])(=[O:4])[CH3:5].[OH:9][CH2:10][CH2:11][Cl:12]>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][Cl:12] | CCN(CC)CC.CS(=O)(=O)Cl.OCCCl | CS(=O)(=O)CS(=O)(=O)OCCCl | null | null | C(C)#N | Oxidation | OtherReaction | 5ff5625b9b80dadb5cd70f9d61f0a4f01259c20af0e162e9aa149626cef6fb8d | d8adddb00d4da01ce543b4b6067a981164ee620a1cd22edfcbe14bd0de7deb95 | null | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-[S;H0;D4;+0:2](-[CH3;D1;+0:3])(=[O;D1;H0:4])=[O;D1;H0:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[CH2;D2;+0:3]-[S;H0;D4;+0:2](-[CH3;D1;+0:1])(=[O;D1;H0:4])=[O;D1;H0:5] | null | [] | null | null | 1 | HOUR | A solution of 133 g (1.32 mol.) of triethylamine in 400 ml of anhydrous acetonitrile was cooled to -30° to -40° C., and a solution of 100 g (0.88 mol.) of methanesulfonyl chloride in anhydrous acetonitrile (67 ml) was added dropwise at a rate that prevented the temperature from rising above -30° C. The mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary amine.Sulfonyl halide | Sulfone.Sulfonate | null | null | null | HCl | C(C)#N | null | 1 | CCN(CC)CC.CS(=O)(=O)Cl.OCCCl>C(C)#N>CS(=O)(=O)CS(=O)(=O)OCCCl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-79c238d7b16349c6ba9878c87b186e20 | CC(=O)c1ccc(O)cc1.ClCCCBr>>CC(=O)c1ccc(OCCCCl)cc1 | OC1=CC=C(C=C1)C(C)=O.BrCCCCl.[OH-].[K+]>>ClCCCOC1=CC=C(C=C1)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:13][cH:14]1.Br[CH2:9][CH2:10][CH2:11][Cl:12]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])[cH:13][cH:14]1 | CC(=O)c1ccc(O)cc1.ClCCCBr | CC(=O)c1ccc(OCCCCl)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 68 | [{"value": 68.0, "product": "ClCCCOC1=CC=C(C=C1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of p-hydroxyacetophenone (50.7 g, 0.37 mol) and 1-bromo-3-chloropropane (160 ml, 1.5 mol) in methanol (250 ml) was added portionwise potassium hydroxide (63 g, 1.12 mol). The mixture was stirred at reflux for 24 hours, cooled to room temperature, filtered through Celite and evaporated in vacuo. The residua... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CO | null | null | CC(=O)c1ccc(O)cc1.ClCCCBr>CO>CC(=O)c1ccc(OCCCCl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d942c39a6e844fd1a0e45833b16e0d3f | ClCCCOc1ccc(-c2cn3ccccc3n2)cc1>>CCCCN(CCCC)CCCOc1ccc(-c2cn3ccccc3n2)cc1 | ClCCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2)C1>>C(CCC)N(CCCC)CCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2)C1 | Cl[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:1][cH:16][c:17](-[c:18]2[n:5][c:25]3[n:20]([cH:19]2)[cH:21][cH:22][cH:23][cH:24]3)[cH:27][cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][n:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3... | ClCCCOc1ccc(-c2cn3ccccc3n2)cc1 | CCCCN(CCCC)CCCOc1ccc(-c2cn3ccccc3n2)cc1 | null | null | C(CCC)NCCCC | Miscellaneous | OtherReaction | 591490c6d5cf2519b6d716180b5ccc013cd7be0b0fd86285c9b63d9b0d4326b6 | dd2fd64966e831a5c6f0bf6fdc3dbb91e77030e61e194c03e38ff8b04df63fff | c1ccc(-c2cn3ccccc3n2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4]-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8](-[c;H0;D3;+0:9]2:[c:10]:[#7;a:11](:[c:12]):[c;H0;D3;+0:13](:[c:14]:[c:15]):[n;H0;D2;+0:16]:2):[cH;D2;+0:17]:[cH;D2;+0:18]:1>>[C:19]-[C:20]-[N;H0;D3;+0:16](-[C:21]-[C:22]-[C:23]-[CH3;D1;+0:18])-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4]-[c;H0;D3;+0:5]1:[c:24]:[... | 192 | [{"value": 93.0, "product": "C(CCC)N(CCCC)CCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 192.0, "product": "C(CCC)N(CCCC)CCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 2-(4-chloropropoxyphenyl)imidazo[1,2-a]-pyridine (5.2 g, 14 mmol) in dibutylamine (30 ml) was stirred at reflux for 5 hours. The excess dibutylamine was removed by distillation and the resulting oil was flash chromatographed (silica gel, 9:1 CH2Cl2 : acetone) to give the free base of the title compound ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether.Tertiary amine | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | null | C(CCC)NCCCC | null | null | ClCCCOc1ccc(-c2cn3ccccc3n2)cc1>C(CCC)NCCCC>CCCCN(CCCC)CCCOc1ccc(-c2cn3ccccc3n2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9efe203deaa442a39739846cd4aff0b2 | CCC(=O)c1ccc(O)cc1.CCCCNCCCC.Cc1cccnc1N.ClCCCBr>>CCCCN(CCCC)CCCOc1ccc(-c2nc3c(C)cccn3c2C)cc1 | CC=1C(=NC=CC1)N.C(CCC)NCCCC.OC1=CC=C(C=C1)C(CC)=O.BrCCCCl.BrBr>>C(CCC)N(CCCC)CCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1C | O=[C:18]([c:17]1[cH:16][cH:15][c:14]([OH:13])[cH:30][cH:29]1)[CH2:27][CH3:28].[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH3:9].[NH2:19][c:20]1[c:21]([CH3:22])[cH:23][cH:24][cH:25][n:26]1.Cl[CH2:10][CH2:11][CH2:12]Br>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][O... | CCC(=O)c1ccc(O)cc1.CCCCNCCCC.Cc1cccnc1N.ClCCCBr | CCCCN(CCCC)CCCOc1ccc(-c2nc3c(C)cccn3c2C)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 45fdad3885031b4160ef11025b59908ff19264a75e5938f66dcbb58594528350 | 3277b3d365a6681ab73086f20be42bfaa9991749dff2a06105284a8ee9d8caef | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-Cl.O=[C;H0;D3;+0:4](-[CH2;D2;+0:5]-[C;D1;H3:6])-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]:[c:13]:1.[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18].[NH2;D1;+0:19]-[c:20](:[c:21]):[n;H0;D2;+0:22]:[c:23]:[c:24]>>[C:14]-[C:15]-[N;H0;D3;+0:16](-[C:17]-[C:18])-[CH2;D2;+0:3]-[C:2... | 62 | [{"value": 62.0, "product": "C(CCC)N(CCCC)CCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | p-Hydroxypropiophenone (50 g, 0.33 mmol) was reacted with 1-bromo-3-chloropropane and the resulting compound reacted with bromine as described in Example 1. The resulting compound was reacted with 3-methyl-2-aminopyridine (1.7 g, 16 mmol) and the product reacted with dibutylamine as described in Example 1 to produce 2.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ketone.Aromatic alcohol.Primary amine.Secondary amine | Ether.Tertiary amine | c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HCl.Br- | null | null | null | CCC(=O)c1ccc(O)cc1.CCCCNCCCC.Cc1cccnc1N.ClCCCBr>>CCCCN(CCCC)CCCOc1ccc(-c2nc3c(C)cccn3c2C)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2f581a38daf94834b468162a35cf8171 | Cc1cccn2cc(C(=O)c3ccc(OCCCCl)cc3)nc12>>CCCCN(CCCC)CCCOc1ccc(C(=O)c2cn3cccc(C)c3n2)cc1 | ClCCCOC1=CC=C(C(=O)C=2N=C3N(C=CC=C3C)C2)C=C1>>C(CCC)N(CCCC)CCCOC1=CC=C(C(=O)C=2N=C3N(C=CC=C3C)C2)C=C1 | Cl[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:1][cH:16][c:17]([C:18](=[O:19])[c:20]2[cH:21][n:5]3[cH:6][cH:24][cH:25][c:26]([CH3:27])[c:28]3[n:29]2)[cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[c:20]2[cH:21][n:22]3[... | Cc1cccn2cc(C(=O)c3ccc(OCCCCl)cc3)nc12 | CCCCN(CCCC)CCCOc1ccc(C(=O)c2cn3cccc(C)c3n2)cc1 | null | null | C(CCC)NCCCC | Miscellaneous | OtherReaction | 591490c6d5cf2519b6d716180b5ccc013cd7be0b0fd86285c9b63d9b0d4326b6 | dd2fd64966e831a5c6f0bf6fdc3dbb91e77030e61e194c03e38ff8b04df63fff | O=C(c1ccccc1)c1cn2ccccc2n1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4]-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8](-[C:9](=[O;D1;H0:10])-[c:11]2:[#7;a:12]:[c;H0;D3;+0:13]3:[c:14](-[C;D1;H3:15]):[c:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[n;H0;D3;+0:19]:3:[cH;D2;+0:20]:2):[cH;D2;+0:21]:[cH;D2;+0:22]:1>>[C:23]-[C:24]-[CH2;D2;+0:18]-[N;H0;D3;+0:19](-[C:25]-[C:26]-[C:27]-[CH... | 197.7 | [{"value": 100.0, "product": "C(CCC)N(CCCC)CCCOC1=CC=C(C(=O)C=2N=C3N(C=CC=C3C)C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 197.7, "product": "C(CCC)N(CCCC)CCCOC1=CC=C(C(=O)C=2N=C3N(C=CC=C3C)C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(4-chloropropoxybenzoyl)-8-methylimidazo-[1,2-a]pyridine (2,4 g, 6.0 mmol) in dibutylamine (30 ml) was stirred at reflux for 8 hours. The excess dibutylamine was removed by distillation and the resulting oil was flash chromatographed (silica gel, acetone) to give the free base of the title compound (2.5 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether.Tertiary amine | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | null | C(CCC)NCCCC | null | null | Cc1cccn2cc(C(=O)c3ccc(OCCCCl)cc3)nc12>C(CCC)NCCCC>CCCCN(CCCC)CCCOc1ccc(C(=O)c2cn3cccc(C)c3n2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e27c01981aec452885615db0b8aa697e | Cc1ccnc(N)c1>>Cc1cn2ccccc2n1 | C(CCC)NCCCC.CC1=CC(=NC=C1)N>>CC=1N=C2N(C=CC=C2)C1 | [CH3:1][c:7]1[cH:6][cH:5][n:4][c:9]([NH2:10])[cH:8]1>>[CH3:1][c:2]1[cH:3][n:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10]1 | Cc1ccnc(N)c1 | Cc1cn2ccccc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6d486165009112780e608dff97176824bff10b35baa5286e796a3ea4a90aee71 | 0c2e6cfe0bdb8f8cd78303a7637b3ef339f807f5bc27c4a22ad516ce20b37476 | c1ccn2ccnc2c1 | [CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[n;H0;D2;+0:5]:[c:6](-[NH2;D1;+0:7]):[c:8]:1>>[CH3;D1;+0:1]-[c:9]1:[c:10]:[n;H0;D3;+0:5]2:[c:4]:[c:3]:[cH;D2;+0:2]:[c:8]:[c:6]:2:[n;H0;D2;+0:7]:1 | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Methyl-2-aminopyridine (1.4 g, 12.5 mmol) was reacted with β-bromo-α-keto-(4-chloropropoxy)propiophenone as described in Example 8. The resulting product was reacted with dibutylamine as described in Example 8 to produce 2.9 g (75% yield) of the free base of the title compound which was converted to the HCl salt, mp ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | Other | null | null | null | Cc1ccnc(N)c1>>Cc1cn2ccccc2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-79b7e20c21f04bd287a87a9adaed0cfb | CCCCN(CCCC)CCCCl.Cc1cccn2c(C(=O)c3ccc(O)cc3)cnc12>>CCCCN(CCCC)CCCOc1ccc(C(=O)c2cnc3c(C)cccn23)cc1 | OC1=CC=C(C(=O)C2=CN=C3N2C=CC=C3C)C=C1.C(CCC)N(CCCC)CCCCl.[OH-].[K+]>>C(CCC)N(CCCC)CCCOC1=CC=C(C(=O)C2=CN=C3N2C=CC=C3C)C=C1 | Cl[CH2:12][CH2:11][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][CH2:8][CH3:9].[OH:13][c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[c:20]2[cH:21][n:22][c:23]3[c:24]([CH3:25])[cH:26][cH:27][cH:28][n:29]23)[cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][O:... | CCCCN(CCCC)CCCCl.Cc1cccn2c(C(=O)c3ccc(O)cc3)cnc12 | CCCCN(CCCC)CCCOc1ccc(C(=O)c2cnc3c(C)cccn23)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)c1cnc2ccccn12 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 31 | [{"value": 31.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(4-hydroxybenzoyl)-8-methylimidazo[1,2-a]-pyridine (2.3 g, 9.6 mmol), dibutylaminopropyl chloride (6.8 g, 33 mmol) and potassium hydroxide (1.3 g, 23 mmol) in methanol (60 ml) was stirred at reflux for 96 hours. The mixture was concentrated and the resulting oil was flash chromatographed (silica gel, 2.5... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccn2ccnc2c1 | HCl | CO | null | null | CCCCN(CCCC)CCCCl.Cc1cccn2c(C(=O)c3ccc(O)cc3)cnc12>CO>CCCCN(CCCC)CCCOc1ccc(C(=O)c2cnc3c(C)cccn23)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d9b4785edab5498986fa0d5639524ba5 | CCCCCCCCN(C)C.CCl>>CCCCCCCC[N+](C)(C)C | CCl.C(CCCCCCC)N(C)C.C[O-].[Na+].CO.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.C(CCCCCCC)O>>C[O-].C(CCCCCCC)[N+](C)(C)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:12].Cl[CH3:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N+:9]([CH3:10])([CH3:11])[CH3:12] | CCCCCCCCN(C)C.CCl | CCCCCCCC[N+](C)(C)C | null | [Cl-].C(CCCCCCC)[N+](C)(C)C | CO | Heteroatom Alkylation and Arylation | OtherReaction | 4fb461fd1d845eeffcd721907fb84dda2a83d6f16d6187a0c591ac1d342a1cfa | 7c33147a6170e63e1fbe1110c4ce069481be57a96b70c4a5a6d7e8253f321bd2 | null | Cl-[CH3;D1;+0:1].[C:2]-[C:3]-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6]>>[C:2]-[C:3]-[N+;H0;D4:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:1] | null | [] | null | null | null | null | One mol of phosphoric anhydride was added to three mols of octyl alcohol over a period of one hour at 60°-70° C. while stirring. They were allowed to react which each other at 70° C. for three hours and a mixture of mono and dioctyl phosphate was obtained. Separately, 0.5 mol of octyl dimethylamine and 200 ml of methan... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | null | null | null | Other | [Cl-].C(CCCCCCC)[N+](C)(C)C.CO | null | null | CCCCCCCCN(C)C.CCl>[Cl-].C(CCCCCCC)[N+](C)(C)C.CO>CCCCCCCC[N+](C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2a2734eb88c143a38c09acebdd4195a1 | CO.COc1ccc(C(O)C(Cl)=C(Cl)Cl)cc1>>COC(=O)/C(Cl)=C/c1ccc(OC)cc1 | COC1=CC=C(C=C1)C(O)C(=C(Cl)Cl)Cl.S(O)(O)(=O)=O.CO.Cl>>COC(/C(=C/C1=CC=C(C=C1)OC)/Cl)=O | [CH3:1][OH:2].Cl[C:3](Cl)=[C:5]([Cl:6])[CH:7]([OH:4])[c:8]1[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])/[C:5]([Cl:6])=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15]1 | CO.COc1ccc(C(O)C(Cl)=C(Cl)Cl)cc1 | COC(=O)/C(Cl)=C/c1ccc(OC)cc1 | null | null | O | Acylation | OtherReaction | 85a9acbb3963c3118be5d9eea104f46e6d1f681a056980835cd756054a03a5ad | 05c3e2fd7be4c52576083ab6610a63b9a558e4326fe2c24a265da529743d42d3 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-Cl)=[C;H0;D3;+0:2](-[Cl;D1;H0:3])-[CH;D3;+0:4](-[OH;D1;+0:5])-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[OH;D1;+0:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;H0;D1;+0:5])/[C;H0;D3;+0:2](-[Cl;D1;H0:3])=[CH;D2;+0:4]/[c:6](:[c:7]):[c:8] | 99 | [{"value": 99.0, "product": "COC(/C(=C/C1=CC=C(C=C1)OC)/Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | p-Methoxyphenyltrichlorovinyl carbinol (2.3 g, 8.6 millimoles) is added to a 40:60 (V/V) solution of sulfuric acid/methanol which is stirred under nitrogen at reflux (100° C.-106° C.) for 7 minutes. Rapid evolution of hydrogen chloride is noted and ceases after this period. The solution is cooled and poured into 40 ml ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Alkenyl halide.Secondary alcohol.Methanol | Alkenyl halide.Ester | null | null | c1ccccc1 | HCl | O | null | null | CO.COc1ccc(C(O)C(Cl)=C(Cl)Cl)cc1>O>COC(=O)/C(Cl)=C/c1ccc(OC)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0456d0b63d08430e9b2503ac98653c65 | COC(=O)/C(Cl)=C/c1ccc(OC)cc1.OC(C(Cl)=C(Cl)Cl)c1ccc(Cl)cc1>>COC(=O)/C(Cl)=C/c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)C(O)C(=C(Cl)Cl)Cl.COC(/C(=C/C1=CC=C(C=C1)OC)/Cl)=O.Cl>>COC(/C(=C/C1=CC=C(C=C1)Cl)/Cl)=O | COc1cc[c:8](/[CH:7]=[C:5](/[C:3]([O:2][CH3:1])=[O:4])[Cl:6])cc1.OC(C(Cl)=C(Cl)Cl)c1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])/[C:5]([Cl:6])=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | COC(=O)/C(Cl)=C/c1ccc(OC)cc1.OC(C(Cl)=C(Cl)Cl)c1ccc(Cl)cc1 | COC(=O)/C(Cl)=C/c1ccc(Cl)cc1 | null | null | null | Miscellaneous | OtherReaction | 863cb6c491b8b6a6d8515759e2616072fce5116ba5532c5823ba4718c1a63042 | b65bf6cd960929e38ef1569ca53784dd79edd5d3795bf9ad77bfbf40d36c41e0 | c1ccccc1 | C-O-c1:c:c:[c;H0;D3;+0:1](/[C:2]=[C:3](\[Cl;D1;H0:4])-[C:5](-[#8:6])=[O;D1;H0:7]):c:c:1.Cl-C(-Cl)=C(-Cl)-C(-O)-c1:[cH;D2;+0:8]:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:1>>[#8:6]-[C:5](=[O;D1;H0:7])/[C:3](-[Cl;D1;H0:4])=[C:2]/[c;H0;D3;+0:1]1:[cH;D2;+0:8]:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:1 | 93 | [{"value": 93.0, "product": "COC(/C(=C/C1=CC=C(C=C1)Cl)/Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | p-Chlorophenyltrichlorovinyl carbinol (6.0 g, 22.0 millimoles) is added to a refluxing solution of methanolic sulfuric acid (30 ml as noted in Example 4). Hydrogen chloride evolution is noted during the stirring procedure for 45 minutes. The mixture is cooled and has a workup as in Example 4, which affords z-methyl-2-c... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Alkenyl halide.Ether.Secondary alcohol | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | null | COC(=O)/C(Cl)=C/c1ccc(OC)cc1.OC(C(Cl)=C(Cl)Cl)c1ccc(Cl)cc1>>COC(=O)/C(Cl)=C/c1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4bb14ca94d854de98c85274ad779da40 | O=C(O)C(=O)Cc1ccccc1[N+](=O)[O-]>>O=C(O)C(O)Cc1ccccc1[N+](=O)[O-] | CN(C=O)C.S(=O)(Cl)Cl.[N+](=O)([O-])C1=C(C=CC=C1)CC(C(=O)O)=O>>OC(C(=O)O)CC1=C(C=CC=C1)[N+](=O)[O-] | [O:1]=[C:2]([OH:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15]>>[O:1]=[C:2]([OH:3])[CH:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15] | O=C(O)C(=O)Cc1ccccc1[N+](=O)[O-] | O=C(O)C(O)Cc1ccccc1[N+](=O)[O-] | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6]-[c:7]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4](-[OH;D1;+0:5])-[C:6]-[c:7] | 95 | [{"value": 95.0, "product": "OC(C(=O)O)CC1=C(C=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To magnetically stirred N,N-dimethylformamide (23 ml., 297.3 mmol) cooled in ice was slowly added dropwise thionyl chloride (139 ml., ca. 1.91 mol). A solution of (+)-α-hydroxy-2-nitrobenzenepropanoic acid [11.60 g., 54.9 mmol, [α]D25 +49.94° (c 2.465, 95% EtOH)], obtained from the chiral reduction of 2-nitro -α-oxoben... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | null | null | null | O=C(O)C(=O)Cc1ccccc1[N+](=O)[O-]>>O=C(O)C(O)Cc1ccccc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bbaa8fd2fc2a4f12ab8b5fe533c40c1c | Nc1ccccc1CC(Cl)C(=O)O>>O=C(O)[C@@H]1Cc2ccccc2N1 | CC1NC(CCC1)C.ClC(C(=O)O)CC1=C(C=CC=C1)N.[OH-].[Na+].Cl>>N1[C@@H](CC2=CC=CC=C12)C(=O)O | Cl[CH:4]([C:2](=[O:1])[OH:3])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12]>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12]1 | Nc1ccccc1CC(Cl)C(=O)O | O=C(O)[C@@H]1Cc2ccccc2N1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | da993167d58388d7e927ece80102774e84bf539eaec6212c7b46fb267c1233b4 | f727fed8b2cf723a92e5af137ab57c7229fb353af6a01a0b7b0aeb3a7b28a8b4 | c1ccc2c(c1)CCN2 | Cl-[CH;D3;+0:1](-[C:2]-[c:3]:[c:4](-[NH2;D1;+0:5]):[c:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[O;D1;H0:8]=[C:7](-[O;D1;H1:9])-[C@@H;D3;+0:1]1-[C:2]-[c:3]:[c:4](:[c:6])-[NH;D2;+0:5]-1 | 74 | [{"value": 74.0, "product": "N1[C@@H](CC2=CC=CC=C12)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (+)-α-Chloro-2-aminobenzenepropanoic acid 2,6-dimethylpiperidine salt (1.25 g., 4.00 mmol) was added to magnetically stirred N sodium hydroxide (4 ml.) under nitrogen. The solution was stirred under nitrogen overnight at room temperature. The pH was adjusted to a value between 2 and 3 (pH paper) with conc. hydrochloric... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary amine | Secondary amine | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HCl | CN(C)C=O | null | 8 | Nc1ccccc1CC(Cl)C(=O)O>CN(C)C=O>O=C(O)[C@@H]1Cc2ccccc2N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bb00c855c12145619bd8ea260945dc3b | O=C(O)C(=O)Cc1ccccc1[N+](=O)[O-]>>O=C(O)C(O)Cc1ccccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C=CC=C1)CC(C(=O)O)=O.N1[C@H](C(=O)O)CCC1.[BH4-].[Na+]>>OC(C(=O)O)CC1=C(C=CC=C1)[N+](=O)[O-] | [O:1]=[C:2]([OH:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15]>>[O:1]=[C:2]([OH:3])[CH:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15] | O=C(O)C(=O)Cc1ccccc1[N+](=O)[O-] | O=C(O)C(O)Cc1ccccc1[N+](=O)[O-] | null | null | O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6]-[c:7]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4](-[OH;D1;+0:5])-[C:6]-[c:7] | null | [] | null | null | 6 | DAY | L-(-)-proline (7.50 g., 65.1 mmol) and sodium borohydride (2.46 g., 65.1 mmol) were stirred in tetrahydrofuran under nitrogen for sixteen hours. Recrystallized o-nitrophenylpyruvic acid (14.17 g., 76.5 mmol) in tetrahydrofuran (50 ml.) was added dropwise, and the resulting solution was stirred at room temperature for s... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | O1CCCC1 | null | 144 | O=C(O)C(=O)Cc1ccccc1[N+](=O)[O-]>O1CCCC1>O=C(O)C(O)Cc1ccccc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4fa3d32004a64365b5c133d511bd3d13 | O=C(O)C(O)Cc1ccccc1[N+](=O)[O-].O=S(Cl)Cl>>O=C(O)C(Cl)Cc1ccccc1[N+](=O)[O-] | S(=O)(Cl)Cl.C[N+](=CCl)C.[Cl-].CC1NC(CCC1)C.OC(C(=O)O)CC1=C(C=CC=C1)[N+](=O)[O-]>>CC1NC(CCC1)C.ClC(C(=O)O)CC1=C(C=CC=C1)[N+](=O)[O-] | O[CH:12]([C:10](=[O:9])[OH:11])[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[N+:21](=[O:22])[O-:23].O=S(Cl)[Cl:13]>>[O:9]=[C:10]([OH:11])[CH:12]([Cl:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[N+:21](=[O:22])[O-:23] | O=C(O)C(O)Cc1ccccc1[N+](=O)[O-].O=S(Cl)Cl | O=C(O)C(Cl)Cc1ccccc1[N+](=O)[O-] | null | null | CN(C=O)C.C(C)O.CCOCC.ClCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[Cl;H0;D1;+0:1]-[CH;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | null | null | 8 | HOUR | To magnetically stirred N,N-dimethylformamide (3 mL) cooled in ice was added slowly dropwise thionyl chloride (4.5 ml., 61.7 mmol) and the resulting cold Vilsmeier reagent was diluted with dichloromethane (30 ml.). (-)-α-Hydroxy-2-nitrobenzenepropanoic acid [3.00 g., 14.2 mmol, [α]D25 -63.04° (c 0.955, 95% ethanol)] in... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1ccccc1 | HCl | CN(C=O)C.C(C)O.CCOCC.ClCCl | null | 8 | O=C(O)C(O)Cc1ccccc1[N+](=O)[O-].O=S(Cl)Cl>CN(C=O)C.C(C)O.CCOCC.ClCCl>O=C(O)C(Cl)Cc1ccccc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9ef1ffbbe2ba4e948cd69ef247efc7ac | NS(=O)(=O)c1ccccc1I>>NS(=O)(=O)c1ccccc1 | CC(C)(C)C(=O)OC=1C=CC(=CC1OC(=O)C(C)(C)C)C(CNC)O.Cl.IC1=C(C=CC=C1)S(=O)(=O)N.P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C1(=CC=CC=C1)S(=O)(=O)N | I[c:10]1[c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:6][cH:7][cH:8][cH:9]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | NS(=O)(=O)c1ccccc1I | NS(=O)(=O)c1ccccc1 | null | Cl[Pd]Cl.[Cu]I | CN(C=O)C.C(C)N(CC)CC | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#16:5]):[c:6]>>[#16:5]-[c:4](:[c:6]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | null | null | To a solution of 28.3 g (0.1 mole) of 2-iodophenylsulfonamide in 350 ml of dimethylformamide and 100 ml of triethylamine are added 1.0 g of palladium dichloro-bis(triphenylphosphite) complex, PdCl2 [P(C6H5)3 ]2, and 0.5 g of copper(I) iodide (CuI). Gaseous propine is then introduced into this solution until the startin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | I- | Cl[Pd]Cl.[Cu]I.CN(C=O)C.C(C)N(CC)CC | null | null | NS(=O)(=O)c1ccccc1I>Cl[Pd]Cl.[Cu]I.CN(C=O)C.C(C)N(CC)CC>NS(=O)(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-30de9da655d044c9895a8b402380e49a | F.FC(F)(F)C(Cl)(Cl)Oc1ccc(Cl)cc1>>FC(F)(F)C(F)(Cl)Oc1ccc(Cl)cc1 | ClC(C(F)(F)F)(OC1=CC=C(C=C1)Cl)Cl.F.[Sb](Cl)(Cl)(Cl)(Cl)Cl>>ClC(C(F)(F)F)(OC1=CC=C(C=C1)Cl)F | [FH:6].Cl[C:5]([C:2]([F:1])([F:3])[F:4])([Cl:7])[O:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1>>[F:1][C:2]([F:3])([F:4])[C:5]([F:6])([Cl:7])[O:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | F.FC(F)(F)C(Cl)(Cl)Oc1ccc(Cl)cc1 | FC(F)(F)C(F)(Cl)Oc1ccc(Cl)cc1 | null | null | null | Miscellaneous | OtherReaction | 6cbceb006a6c2bb4630a1bd9846208a4cd5d1f25fdbb5d103e5ad794516c8409 | 842a324f59ad0063075fe3cc48957e60bf881790a58fdb16332fd28d26a3c247 | c1ccccc1 | Cl-[C;H0;D4;+0:1](-[Cl;D1;H0:2])(-[#8:3]-[c:4])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[FH;D0;+0:9]>>[Cl;D1;H0:2]-[C;H0;D4;+0:1](-[F;H0;D1;+0:9])(-[#8:3]-[c:4])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8] | 89.8 | [{"value": 89.8, "product": "ClC(C(F)(F)F)(OC1=CC=C(C=C1)Cl)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A 500 ml polytetrafluoroethylene reactor equipped with stirrer, thermometer and reflux condenser is charged with 55.9 g (0.2 mol) of 4-(1,1-dichloro-2,2,2-trifluoroethoxy)chlorobenzene in 100 ml of hydrogen fluoride. 3.0 g (0.01 mol; corresponding to 5 mol%) of antimony pentachloride are added at a temperature in the r... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ether | Tertiary halide.Tertiary halide | null | null | c1ccccc1 | HCl | null | null | 0.333333 | F.FC(F)(F)C(Cl)(Cl)Oc1ccc(Cl)cc1>>FC(F)(F)C(F)(Cl)Oc1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-53a85923a86c4172acc0fb7d8d5d8d30 | F.FC(F)(F)CSC1C=CC=CC1(Cl)Cl>>FC(Sc1ccccc1Cl)C(F)(F)F | ClC1(C(C=CC=C1)SCC(F)(F)F)Cl.F.[Sb](Cl)(Cl)(Cl)(Cl)Cl>>ClC1=C(C=CC=C1)SC(C(F)(F)F)F | [FH:1].Cl[C:9]1([Cl:10])[CH:4]([S:3][CH2:2][C:11]([F:12])([F:13])[F:14])[CH:5]=[CH:6][CH:7]=[CH:8]1>>[F:1][CH:2]([S:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[Cl:10])[C:11]([F:12])([F:13])[F:14] | F.FC(F)(F)CSC1C=CC=CC1(Cl)Cl | FC(Sc1ccccc1Cl)C(F)(F)F | null | null | null | Miscellaneous | OtherReaction | 8402e41d077c1491268f1c52e4ddce02c4e4bf14a63bd67ec224c8f5d2505e56 | 12c1c5c7dbba2ebea84dd1caaef720a655528dfbfbb69e7ad822d7d7004aede8 | c1ccccc1 | Cl-[C;H0;D4;+0:1]1(-[Cl;D1;H0:2])-[CH;D2;+0:3]=[CH;D2;+0:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-[CH;D3;+0:7]-1-[#16:8]-[CH2;D2;+0:9]-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13].[FH;D0;+0:14]>>[Cl;D1;H0:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7]:1-[#16:8]-[CH;D3;+0:9](-[F;H0;D1;+0:... | null | [] | null | null | 3 | HOUR | A 500 ml polytetrafluoroethylene reactor equipped with stirrer, thermometer and reflux condenser is charged with 24.7 g (0.094 mol) of 1,1-dichloro-2,2,2-trifluoroethylthiobenzene which are subsequently condensed with 50 g of hydrogen fluoride. 4.2 g (0.014 mol; corresponding to 15 mol%) of antimony pentachloride are a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Monosulfide.Conjugated diene | Aromatic halide.Secondary halide.Monosulfide | C1=CCCC=C1 | c1ccccc1 | c1ccccc1 | HCl | null | null | 3 | F.FC(F)(F)CSC1C=CC=CC1(Cl)Cl>>FC(Sc1ccccc1Cl)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-444e854447fe4b53ac481a298adcab6e | CC(=O)OC(C)=O.CC(=O)OC(C)=O.Cc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1>>CC(=O)OC(OC(C)=O)c1ccc(C(OC(C)=O)(C(F)(F)F)C(F)(F)F)cc1 | C(C)(=O)OC(C)=O.FC(C(C(F)(F)F)(O)C1=CC=C(C=C1)C)(F)F.S(O)(O)(=O)=O.C(C)(=O)OC(C)=O>>C(C)(=O)OC(C1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)OC(C)=O)OC(C)=O | CC(=O)[O:6][C:16]([CH3:17])=[O:18].[CH3:1][C:2](=[O:3])[O:4][C:7]([CH3:8])=[O:9].[CH3:5][c:10]1[cH:11][cH:12][c:13]([C:14]([OH:15])([C:19]([F:20])([F:21])[F:22])[C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]1>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([O:6][C:7]([CH3:8])=[O:9])[c:10]1[cH:11][cH:12][c:13]([C:14]([O:15][C:16]([CH3:17... | CC(=O)OC(C)=O.CC(=O)OC(C)=O.Cc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1 | CC(=O)OC(OC(C)=O)c1ccc(C(OC(C)=O)(C(F)(F)F)C(F)(F)F)cc1 | null | [O-2].[O-2].[O-2].[Cr+6] | O | Acylation | OtherReaction | e7c92516b0703c73b4cb5fc5ac135249bfe4433a15f56fb3a6c1b91a8643705c | 947488b7a4710cdb02433043d0982d6a7d3fbc564a4baa56670ebffc3bd3e1dd | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[O;D1;H0:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;D1;H0:11].[CH3;D1;+0:12]-[c:13](:[c:14]):[c:15].[F;D1;H0:16]-[C:17](-[F;D1;H0:18])(-[F;D1;H0:19])-[C:20](-[OH;D1;+0:21])(-[c:22])-[C:23](-[F;D1;H0:24])(-[F;D1;H0:25])-[F;D1;H0:... | null | [] | null | null | 2 | HOUR | To a solution of 156 g (0.60 mole) of 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]toluene in 675 ml of acetic anhydride is added 135 ml of concentrated sulfuric acid at 0°. To the solution stirred at 0° is added a soluton of 168 g (1.68 mole) of chromium trioxide in 750 ml of acetic anhydride dropwise over a ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Anhydride.Tertiary alcohol | Ester.Ester.Ester | null | null | c1ccccc1 | HO- | [O-2].[O-2].[O-2].[Cr+6].O | null | 2 | CC(=O)OC(C)=O.CC(=O)OC(C)=O.Cc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1>[O-2].[O-2].[O-2].[Cr+6].O>CC(=O)OC(OC(C)=O)c1ccc(C(OC(C)=O)(C(F)(F)F)C(F)(F)F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e7b09e39e6d0482c831f6c8380c5c8e2 | CC(=O)OC(OC(C)=O)c1ccc(C(OC(C)=O)(C(F)(F)F)C(F)(F)F)cc1>>CC(=O)OC(c1ccc(C=O)cc1)(C(F)(F)F)C(F)(F)F | C(C)O.C(C)(=O)OC(C1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)OC(C)=O)OC(C)=O.S(O)(O)(=O)=O>>C(C)(=O)OC(C(F)(F)F)(C(F)(F)F)C1=CC=C(C=O)C=C1 | CC(=O)O[CH:10]([c:9]1[cH:8][cH:7][c:6]([C:5]([O:4][C:2]([CH3:1])=[O:3])([C:14]([F:15])([F:16])[F:17])[C:18]([F:19])([F:20])[F:21])[cH:13][cH:12]1)[O:11]C(C)=O>>[CH3:1][C:2](=[O:3])[O:4][C:5]([c:6]1[cH:7][cH:8][c:9]([CH:10]=[O:11])[cH:12][cH:13]1)([C:14]([F:15])([F:16])[F:17])[C:18]([F:19])([F:20])[F:21] | CC(=O)OC(OC(C)=O)c1ccc(C(OC(C)=O)(C(F)(F)F)C(F)(F)F)cc1 | CC(=O)OC(c1ccc(C=O)cc1)(C(F)(F)F)C(F)(F)F | null | null | O | Miscellaneous | Acetal hydrolysis to aldehyde | 99d6216d1e6a4ec3705c86679722b6c1ba2e1e83ea661cfbae8473cd3c1cd7da | 5d4585057e84f16a9a41a81f9ae63243c1ba7e24e54ff5744f2d5edb4f856efa | c1ccccc1 | C-C(=O)-O-[CH;D3;+0:1](-[O;H0;D2;+0:2]-C(-C)=O)-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[c:5] | 89.1 | [{"value": 89.1, "product": "C(C)(=O)OC(C(F)(F)F)(C(F)(F)F)C1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 130 ml of ethanol are added 60 g (0.15 mole) of α,α-bis-acetyloxy-4-[1-(acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]toluene and 13.5 ml of concentrated sulfuric acid in 135 ml of water. The resulting solution is stirred and heated at reflux for thirty minutes. The solution is then cooled and extracted with 1... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Aldehyde | null | null | c1ccccc1 | HO- | O | null | null | CC(=O)OC(OC(C)=O)c1ccc(C(OC(C)=O)(C(F)(F)F)C(F)(F)F)cc1>O>CC(=O)OC(c1ccc(C=O)cc1)(C(F)(F)F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d619ebd614624d4388075e24b6d34182 | COC(=O)C(c1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1)C(C)Br>>CC(=CC(=O)O)c1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1 | CCOCC.BrC(C(C(=O)OC)C1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O)C.O1CCCC1>>CC(=CC(=O)O)C1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O | C[O:6][C:4]([CH:3]([CH:2](Br)[CH3:1])[c:7]1[cH:8][cH:9][c:10]([C:11]([OH:12])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1)=[O:5]>>[CH3:1][C:2](=[CH:3][C:4](=[O:5])[OH:6])[c:7]1[cH:8][cH:9][c:10]([C:11]([OH:12])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1 | COC(=O)C(c1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1)C(C)Br | CC(=CC(=O)O)c1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1 | null | null | null | Miscellaneous | OtherReaction | 2e5688f8c1aa40dce78bf69bd3bcf8baf2169534ff96670d7e6dadeca72a567f | 062fc4dd58455c891e367b9166799a0526e52d510556dcf9aea549d31460a90c | c1ccccc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[CH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | null | [] | null | null | null | null | To a solution of methyl 3-bromo-3-methyl-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}propanoate in tetrahydrofuran can be added an equivalent amount of 1,5-diazabicyclo[3.4.0]nonene-5. The resulting reaction mixture can be stirred at elevated temperature until thin layer chromatographic analysis of a ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | null | null | null | COC(=O)C(c1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1)C(C)Br>>CC(=CC(=O)O)c1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-faaf68394c7640afbc0442dba1d6486f | O=C(O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1.O=[N+]([O-])O>>O=C(O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1[N+](=O)[O-] | O.[N+](=O)(O)[O-].FC(C(C(F)(F)F)(O)C1=CC=C(C=C1)CCC(=O)O)(F)F.[N+](=O)(O)[O-]>>[N+](=O)([O-])C1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)O | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1.O[N+:22](=[O:23])[O-:24]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19])[cH:20][c:21]1[N... | O=C(O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1.O=[N+]([O-])O | O=C(O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1[N+](=O)[O-] | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | 18 | HOUR | To a solution of 63.2 g (0.20 mole) of 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid in 160 ml of concentrated sulfuric acid is added 40 ml of fuming nitric acid (90%) dropwise with stirring at 0°-5°. Following the nitric acid addition the solution is allowed to warm to 20° with stirring o... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | S(O)(O)(=O)=O | null | 18 | O=C(O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1.O=[N+]([O-])O>S(O)(O)(=O)=O>O=C(O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-325adc1ebbbf4db88aa4a692c9efebaa | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1.O=S(=O)(O)Cl>>COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1S(=O)(=O)Cl | ClS(=O)(=O)O.FC(C(C(F)(F)F)(O)C1=CC=C(C=C1)CCC(=O)OC)(F)F>>ClS(=O)(=O)C1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11]([OH:12])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1.O[S:23](=[O:24])(=[O:25])[Cl:26]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11]([OH:12])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[... | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1.O=S(=O)(O)Cl | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1S(=O)(=O)Cl | null | null | null | Heteroatom Alkylation and Arylation | Aromatic sulfonyl chlorination | 04bb0e110ac9bc3104a40572864ecdd042b39019cff0ea96d1a0ad7c9eb6ecf3 | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1ccccc1 | O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4]):[c:9]:[c:10] | null | [] | null | null | null | null | To excess chlorosulfonic acid cooled with an ice-acetone bath can be added methyl 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoate with stirring. The solution should be stirred for several hours. Addition of the reaction mixture to ice and isolation of the product will give 2-chlorosulfonyl-4-[2,... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1.O=S(=O)(O)Cl>>COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1S(=O)(=O)Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-74e636509a9640c291269b22cc9cdee6 | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1S(=O)(=O)Cl>>COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1S | ClS(=O)(=O)C1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC>>SC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC | O=[S:23](=O)(Cl)[c:22]1[c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:8][cH:9][c:10]([C:11]([OH:12])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20])[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11]([OH:12])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20])[cH:21][c:... | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1S(=O)(=O)Cl | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1S | null | [Zn] | C(C)(=O)O | Reduction | OtherReaction | 67c58f2128339179ba957163c48f4a4ad5eac877ca5a6bdb7ff20914d4efc174 | fdaccf528edde07917e32c5a4cba468523458b8901959f3cb21411d1f4e7837a | c1ccccc1 | Cl-[S;H0;D4;+0:1](=O)(=O)-[c:2](:[c:3]):[c:4]>>[SH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To excess chlorosulfonic acid cooled with an ice-acetone bath can be added methyl 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoate with stirring. The solution should be stirred for several hours. Addition of the reaction mixture to ice and isolation of the product will give 2-chlorosulfonyl-4-[2,... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Aromatic thiol | null | null | c1ccccc1 | Other | [Zn].C(C)(=O)O | null | null | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1S(=O)(=O)Cl>[Zn].C(C)(=O)O>COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2f5977fcdfc64a0bba0973c2c4fe06ab | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1SC>>CSc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1CCC(=O)O | CSC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC.Cl>>CSC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)O | C[O:23][C:21]([CH2:20][CH2:19][c:18]1[c:3]([S:2][CH3:1])[cH:4][c:5]([C:6]([OH:7])([C:8]([F:9])([F:10])[F:11])[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1)=[O:22]>>[CH3:1][S:2][c:3]1[cH:4][c:5]([C:6]([OH:7])([C:8]([F:9])([F:10])[F:11])[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][c:18]1[CH2:19][CH2:20][C:21](=[O:22])[OH:2... | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1SC | CSc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1CCC(=O)O | null | null | [OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | To a solution of 3,4-dihydro-7-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2H-1-benzothiapyran-2-one in dimethylacetamide can be added a one molar excess of sodium hydroxide in methanol. The resulting solution should be heated, and a one molar excess of methyl iodide should be added with stirring. From the res... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | [OH-].[Na+] | null | null | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1SC>[OH-].[Na+]>CSc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1CCC(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e1c66fb4adac4f998bb29ae2b4de9a65 | COc1cccc(Br)c1.O=C(C(F)(F)F)C(F)(F)F>>COc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 | BrC=1C=C(C=CC1)OC.BrCCBr.BrC=1C=C(C=CC1)OC.FC(C(=O)C(F)(F)F)(F)F.FC(C(=O)C(F)(F)F)(F)F.FC(C(=O)C(F)(F)F)(F)F.Cl.[Mg]>>COC1=CC(=CC=C1)C(C(F)(F)F)(C(F)(F)F)O | Br[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18]1.[C:8](=[O:9])([C:10]([F:11])([F:12])[F:13])[C:14]([F:15])([F:16])[F:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]([OH:9])([C:10]([F:11])([F:12])[F:13])[C:14]([F:15])([F:16])[F:17])[cH:18]1 | COc1cccc(Br)c1.O=C(C(F)(F)F)C(F)(F)F | COc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 | null | null | CCOCC.O.O1CCCC1 | C-C Coupling | Grignard_alcohol | 23831eb2f5100c758a065f977b2daac4728a2009a2a7f37e9b01c50283e9e583 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]>>[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12](-[F;D1;H0:13])(-[... | null | [] | null | null | 18 | HOUR | To a suspension of 13.5 g (0.55 g atoms) of sublimed magnesium chips in 25 ml of anhydrous tetrahydrofuran in a reaction flask fitted with a water-cooled condenser are added 10 g (0.05 mole) of 3-bromo-1-methoxybenzene and 0.5 ml of 1,2-dibromoethane. The resulting reaction mixture is stirred and heated gently until a ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | CCOCC.O.O1CCCC1 | null | 18 | COc1cccc(Br)c1.O=C(C(F)(F)F)C(F)(F)F>CCOCC.O.O1CCCC1>COc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5aad24de5b32448bacb79951b467fed3 | COc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1>>COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=O | COC1=CC(=CC=C1)C(C(F)(F)F)(C(F)(F)F)O.COC(Cl)Cl.Cl>>COC1=C(C=O)C=CC(=C1)C(C(F)(F)F)(O)C(F)(F)F | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([OH:7])([C:8]([F:9])([F:10])[F:11])[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([OH:7])([C:8]([F:9])([F:10])[F:11])[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][c:18]1[CH:19]=[O:20] | COc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 | COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=O | null | [Ti](Cl)(Cl)(Cl)Cl | ClCCl.O | Miscellaneous | OtherReaction | c25c41cbe22c67cd8a516e3f8fc0980bea758f12933876480aae20d5765822e2 | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccccc1 | [#8:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C:7]=[O;D1;H0:8]):[c:5]:[c:6] | 48 | [{"value": 48.0, "product": "COC1=C(C=O)C=CC(=C1)C(C(F)(F)F)(O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 31.6 g (0.12 mole) of 1-methoxy-3-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzene in 200 ml dichloromethane is added 38 g (0.2 mole) of titanium tetrachloride at 0°-5° with stirring under a nitrogen atmosphere. After the resulting solution is stirred for 15 minutes, 11.5 g (0.1 mole) of α,α... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Ti](Cl)(Cl)(Cl)Cl.ClCCl.O | null | 18 | COc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1>[Ti](Cl)(Cl)(Cl)Cl.ClCCl.O>COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ec0779edb24c45fe9d209facc9386718 | COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=O.O=C(O)CC(=O)O>>COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=CC(=O)O | COC1=C(C=O)C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O.C(CC(=O)O)(=O)O.N1CCCCC1>>COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)C=CC(=O)O | O=[CH:19][c:18]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6]([OH:7])([C:8]([F:9])([F:10])[F:11])[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1.O=C(O)[CH2:20][C:21](=[O:22])[OH:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([OH:7])([C:8]([F:9])([F:10])[F:11])[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][c:18]1[CH:19]=[CH:20][C:21](=[O:22... | COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=O.O=C(O)CC(=O)O | COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=CC(=O)O | null | null | N1=CC=CC=C1 | C-C Coupling | OtherReaction | 0c2382c2f7ea556671f2a3c58036f5e0661a08f7658c9ccbb421e2a9daac089b | a6032dd2ea62d1cf56f5cee7663c80211fe5b6aa714acc87461f75a8053630fd | c1ccccc1 | O-C(=O)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[O;D1;H1:4])-[CH;D2;+0:1]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 61 | [{"value": 61.0, "product": "COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)C=CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 15 g (0.05 mole) 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzaldehyde in 50 ml of pyridine are added 11 g (0.11 mole) of malonic acid and 1 g of piperidine. The solution is stirred and gradually heated to 80°. Heating and stirring are continued for 1 hour at 80°. The solution is... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid | null | null | null | c1ccccc1 | HO- | N1=CC=CC=C1 | null | 1 | COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=O.O=C(O)CC(=O)O>N1=CC=CC=C1>COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=CC(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5311bd096d1c45b1920e980fa0c4e746 | COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=CC(=O)O>>COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1CCC(=O)O | COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)C=CC(=O)O>>COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)O | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([OH:7])([C:8]([F:9])([F:10])[F:11])[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][c:18]1[CH:19]=[CH:20][C:21](=[O:22])[OH:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([OH:7])([C:8]([F:9])([F:10])[F:11])[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][c:18]1[CH2:19][CH2:20][C:21](=[O:22])[OH:23] | COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=CC(=O)O | COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1CCC(=O)O | null | null | C(C)O | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 80.9 | [{"value": 80.9, "product": "COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 100 ml of ethanol are added 8.8 g (0.025 mole) of 3-{2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid to produce a solution which is added to a pressure bottle and flushed with nitrogen. To the solution is added 1 g of 10% palladium on carbon. The pressure bottle is placed in ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(C)O | null | null | COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1C=CC(=O)O>C(C)O>COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1CCC(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0960a3e8f0f94a8c9c664b1b2f395258 | CO.COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1CCC(=O)O>>COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1OC | CO.COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)O.S(O)(O)(=O)=O>>COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11]([OH:12])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20])[cH:21][c:22]1[O:23][CH3:24]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11]([OH:12])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20])[cH:21][c:2... | CO.COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1CCC(=O)O | COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1OC | null | null | C1(=CC=CC=C1)C | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[OH;D1;+0:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[C;D1;H3:5] | null | [] | null | null | null | null | To a solution of 50 ml of methanol in 50 ml toluene are added 7.0 g (0.02 mole) of 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid and 1 ml of concentrated sulfuric acid. The resulting solution is stirred, heated at reflux for 18 hours, then concentrated to 20 ml at reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CO.COc1cc(C(O)(C(F)(F)F)C(F)(F)F)ccc1CCC(=O)O>C1(=CC=CC=C1)C>COC(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6f660a7817ea40438cb69e468c18825b | CI.CN(C)C(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1[N+](=O)[O-]>>COC(c1ccc(CCC(=O)N(C)C)c([N+](=O)[O-])c1)(C(F)(F)F)C(F)(F)F | CI.[H-].[Na+].[N+](=O)([O-])C1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)N(C)C.C(C)O>>[N+](=O)([O-])C1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)OC)CCC(=O)N(C)C | I[CH3:1].[OH:2][C:3]([c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][C:10](=[O:11])[N:12]([CH3:13])[CH3:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1)([C:20]([F:21])([F:22])[F:23])[C:24]([F:25])([F:26])[F:27]>>[CH3:1][O:2][C:3]([c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][C:10](=[O:11])[N:12]([CH3:13])[CH3:14])[c:15]([N+:16](=[O:17])[O... | CI.CN(C)C(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1[N+](=O)[O-] | COC(c1ccc(CCC(=O)N(C)C)c([N+](=O)[O-])c1)(C(F)(F)F)C(F)(F)F | null | null | CN(C=O)C.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | cd10a9010f842ab825b304bd2965f17f9c39c4c64e5fc6cd91306ae51817de0d | 9271b713ded6954f3329c61a211042ac37c82b3aff1b62cb455035e69339dd27 | c1ccccc1 | I-[CH3;D1;+0:1].[F;D1;H0:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[C:6](-[OH;D1;+0:7])(-[c:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12]>>[CH3;D1;+0:1]-[O;H0;D2;+0:7]-[C:6](-[c:8])(-[C:3](-[F;D1;H0:2])(-[F;D1;H0:4])-[F;D1;H0:5])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12] | null | [] | null | null | null | null | To a suspension of 2.15 (0.085 mole) of sodium hydride in 200 ml dimethylformamide is added 29.1 g (0.075 mole) of 3-{2-nitro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-N,N-dimethylpropanamide in in 50 ml dimethylformamide at such a rate that excessive foaming is avoided. To the resulting suspension,... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Ether | null | null | c1ccccc1 | HI | CN(C=O)C.O | null | null | CI.CN(C)C(=O)CCc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1[N+](=O)[O-]>CN(C=O)C.O>COC(c1ccc(CCC(=O)N(C)C)c([N+](=O)[O-])c1)(C(F)(F)F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-23f42f8623e741769a45a5605a83b535 | O=C(O)Cc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1>>OCCc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 | FC(C(C(F)(F)F)(O)C=1C=C(C=CC1)CC(=O)O)(F)F.Cl.[H][H]>>FC(C(C(F)(F)F)(O)C=1C=C(C=CC1)CCO)(F)F | O=[C:2]([OH:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([OH:10])([C:11]([F:12])([F:13])[F:14])[C:15]([F:16])([F:17])[F:18])[cH:19]1>>[OH:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([OH:10])([C:11]([F:12])([F:13])[F:14])[C:15]([F:16])([F:17])[F:18])[cH:19]1 | O=C(O)Cc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 | OCCc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3]-[c:4]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[C:3]-[c:4] | 38.9 | [{"value": 38.9, "product": "FC(C(C(F)(F)F)(O)C=1C=C(C=CC1)CCO)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To one liter of 1M borane-tetrahydrofuran complex was added a solution of 100 g (0.33 mole) of 3-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzeneactic acid in 200 ml of tetrahydrofuran. The solution is refluxed for 16 hours under nitrogen. The solution is then refluxed with 400 ml of 6N hydrochloric acid unt... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1 | null | null | O=C(O)Cc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1>O1CCCC1>OCCc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a92e3cb04a4c44e3b5b26d5940e91aac | N.O=[N+]([O-])c1cc2c(c([N+](=O)[O-])c1)OCC2>>Nc1c(CCO)cc([N+](=O)[O-])cc1[N+](=O)[O-] | N.[N+](=O)([O-])C=1C=C(C2=C(CCO2)C1)[N+](=O)[O-].N>>NC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])CCO | [NH3:1].[c:2]12[c:3]([cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16])[CH2:4][CH2:5][O:6]2>>[NH2:1][c:2]1[c:3]([CH2:4][CH2:5][OH:6])[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16] | N.O=[N+]([O-])c1cc2c(c([N+](=O)[O-])c1)OCC2 | Nc1c(CCO)cc([N+](=O)[O-])cc1[N+](=O)[O-] | null | null | C(=O)N | Heteroatom Alkylation and Arylation | OtherReaction | 24a8aa98ea4b138beed710c2dd2b7e94d3484ed8bd12c7cd785386be788cc67a | 10642a6ebaaa1448d06340590fc3ea6841ffa4c71e268d51eace72898564c2ca | c1ccccc1 | [#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[c:5](:[c:6])-[C:7]-[C:8]-[O;H0;D2;+0:9]-1.[NH3;D0;+0:10]>>[#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[NH2;D1;+0:10]):[c:5](-[C:7]-[C:8]-[OH;D1;+0:9]):[c:6] | null | [] | 110 | CELSIUS | null | null | 0.17 Mole (35.7 g) of 2,3-dihydro-5,7-dinitrobenzofuran, prepared according to Chatelus Ann. Chim. [12], 4,505-547 (1949), is suspended in 350 ml of 20% strength ammonia solution and 220 ml of formamide. After 8 hours' heating at 110° C., a further 100 ml of 20% strength ammonia solution are added. Heating is maintaine... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol.Primary amine | c1ccc2c(c1)CCO2 | c1ccccc1 | c1ccccc1 | null | C(=O)N | 110 | null | N.O=[N+]([O-])c1cc2c(c([N+](=O)[O-])c1)OCC2>C(=O)N>Nc1c(CCO)cc([N+](=O)[O-])cc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e4c770bdf0d9415a9eb6b135abc8f215 | NCCO.O=[N+]([O-])c1cc2c(c([N+](=O)[O-])c1)OCC2>>O=[N+]([O-])c1cc(CCO)c(NCCO)c([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C2=C(CCO2)C1)[N+](=O)[O-].NCCO>>OCCNC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])CCO | [NH2:11][CH2:12][CH2:13][OH:14].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[c:10]([c:15]([N+:16](=[O:17])[O-:18])[cH:19]1)[O:9][CH2:8][CH2:7]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([CH2:7][CH2:8][OH:9])[c:10]([NH:11][CH2:12][CH2:13][OH:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1 | NCCO.O=[N+]([O-])c1cc2c(c([N+](=O)[O-])c1)OCC2 | O=[N+]([O-])c1cc(CCO)c(NCCO)c([N+](=O)[O-])c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | b24e0ea252c670da45f2c12df08b1960f84bcf6fa77abfb845213ed2c4543985 | d7adf528712633f83e6bae148cdd27bcd1da32e03c86fb5a52b2cfb0297b6748 | c1ccccc1 | [#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[c:5](:[c:6])-[C:7]-[C:8]-[O;H0;D2;+0:9]-1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[NH;D2;+0:12]-[C:11]-[C:10]):[c:5](-[C:7]-[C:8]-[OH;D1;+0:9]):[c:6] | null | [] | null | null | null | null | 0.29 Mole (60.9 g) of 2,3-dihydro-5,7-dinitrobenzofuran is added in small portions at room temperature to 122 ml of 2-aminoethanol. After the addition is complete, the reaction medium is brought for 15 minutes to 95° C. 500 ml of water are added; after the mixture is cooled, the expected product is drained, and this, a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Primary alcohol.Secondary amine | c1ccc2c(c1)CCO2 | c1ccccc1 | c1ccccc1 | null | O | null | null | NCCO.O=[N+]([O-])c1cc2c(c([N+](=O)[O-])c1)OCC2>O>O=[N+]([O-])c1cc(CCO)c(NCCO)c([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5155b74041e040c5848aa97537ebe3cb | CC1Cc2cc([N+](=O)[O-])cc([N+](=O)[O-])c2O1.N>>CC(O)Cc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1N | [N+](=O)([O-])C=1C=C(C2=C(CC(O2)C)C1)[N+](=O)[O-].N.COCCO>>NC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])CC(C)O | [CH3:1][CH:2]1[O:3][c:16]2[c:5]([cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]2[N+:13](=[O:14])[O-:15])[CH2:4]1.[NH3:17]>>[CH3:1][CH:2]([OH:3])[CH2:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]1[NH2:17] | CC1Cc2cc([N+](=O)[O-])cc([N+](=O)[O-])c2O1.N | CC(O)Cc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1N | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | b9645d4be24e8bef17d95fe9ef844ab65d6e908840b53a61f48178de893a44e4 | 2cc1049c9dc921d9b8eaebe5bfda8bea348225850bbf2fd843a9e1f05f422894 | c1ccccc1 | [#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[c:5](:[c:6])-[C:7]-[C:8](-[C;D1;H3:9])-[O;H0;D2;+0:10]-1.[NH3;D0;+0:11]>>[#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[NH2;D1;+0:11]):[c:5](-[C:7]-[C:8](-[C;D1;H3:9])-[OH;D1;+0:10]):[c:6] | null | [] | 70 | CELSIUS | null | null | 0.39 Mole (88 g) of 2,3-dihydro-5,7-dinitro-2-methylbenzofuran, prepared according to J.A.C.S. 80, p. 4711-4714 (1958), is suspended in 1.1 l of 20% strength ammonia solution and 600 ml of Methyl Cellosolve. After 18 hours' heating at 70° C., the reaction mixture is cooled. The precipitate formed is drained and, after ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol.Primary amine | c1ccc2c(c1)CCO2 | c1ccccc1 | c1ccccc1 | null | O | 70 | null | CC1Cc2cc([N+](=O)[O-])cc([N+](=O)[O-])c2O1.N>O>CC(O)Cc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-52be2b750bf64c28aee0f8bfed4840c7 | CC1Cc2cc([N+](=O)[O-])cc([N+](=O)[O-])c2O1.CN>>CNc1c(CC(C)O)cc([N+](=O)[O-])cc1[N+](=O)[O-] | [N+](=O)([O-])C=1C=C(C2=C(CC(O2)C)C1)[N+](=O)[O-].CN>>CNC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])CC(C)O | [c:3]12[c:4]([cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[N+:16](=[O:17])[O-:18])[CH2:5][CH:6]([CH3:7])[O:8]2.[CH3:1][NH2:2]>>[CH3:1][NH:2][c:3]1[c:4]([CH2:5][CH:6]([CH3:7])[OH:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[N+:16](=[O:17])[O-:18] | CC1Cc2cc([N+](=O)[O-])cc([N+](=O)[O-])c2O1.CN | CNc1c(CC(C)O)cc([N+](=O)[O-])cc1[N+](=O)[O-] | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 0fe390b9bc848b8b0bb983a36ab8baa599ce53655fa07f9b7bc8f136ff5b6b07 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccccc1 | [#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[c:5](:[c:6])-[C:7]-[C:8](-[C;D1;H3:9])-[O;H0;D2;+0:10]-1.[C;D1;H3:11]-[NH2;D1;+0:12]>>[#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[NH;D2;+0:12]-[C;D1;H3:11]):[c:5](-[C:7]-[C:8](-[C;D1;H3:9])-[OH;D1;+0:10]):[c:6] | null | [] | null | null | 10 | HOUR | 0.056 Mole (12.5 g) of 2,3-dihydro-5,7-dinitro-2-methyl-benzofuran is suspended in 100 ml of a 33% strength solution of methylamine in ethanol. After 10 hours' stirring at room temperature in a sealed Erlenmeyer, the reaction mixture is brought for 30 minutes to the refluxing temperature of the alcohol. After the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | c1ccc2c(c1)CCO2 | c1ccccc1 | c1ccccc1 | null | C(C)O | null | 10 | CC1Cc2cc([N+](=O)[O-])cc([N+](=O)[O-])c2O1.CN>C(C)O>CNc1c(CC(C)O)cc([N+](=O)[O-])cc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0f00b2a48ac44f1f81b28c45b15724f2 | Nc1c(CCO)cc([N+](=O)[O-])cc1[N+](=O)[O-]>>Nc1cc([N+](=O)[O-])cc(CCO)c1N | NC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])CCO.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[S]>>NC1=C(C=C(C=C1N)[N+](=O)[O-])CCO | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([CH2:10][CH2:11][OH:12])[c:13]1[NH2:14]>>[NH2:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([CH2:10][CH2:11][OH:12])[c:13]1[NH2:14] | Nc1c(CCO)cc([N+](=O)[O-])cc1[N+](=O)[O-] | Nc1cc([N+](=O)[O-])cc(CCO)c1N | null | null | C(C)(C)O.O | Functional Group Interconversion | Reduction of nitro groups to amines | 5c1ea979989295c14f1f65f49e58974d5c524451abca65fc2e6cec44e3d0784f | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a suspension of 0.119 mole (27 g) of 2-(2-amino-3,5-dinitrophenyl)ethanol obtained in Example 1 in 67.5 ml of isopropanol to which an equal volume of water has been added, a solutionof 38.4 g of sodium sulphide nonahydrate and 5.4 g of sulphur in 10 ml of water is added dropwise at 60°-65° C. Heating is maintained f... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)(C)O.O | null | null | Nc1c(CCO)cc([N+](=O)[O-])cc1[N+](=O)[O-]>C(C)(C)O.O>Nc1cc([N+](=O)[O-])cc(CCO)c1N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-12421d0797394bc59f5eb474f7a37fd6 | ClCCCCl.[Li][P](c1ccccc1)c1ccccc1>>ClCCCP(c1ccccc1)c1ccccc1 | P(C1=CC=CC=C1)C1=CC=CC=C1.[Li]P(C1=CC=CC=C1)C1=CC=CC=C1.ClCCCCl.C(CCC)[Li]>>P(C1=CC=CC=C1)(C1=CC=CC=C1)CCCCl | Cl[CH2:4][CH2:3][CH2:2][Cl:1].[Li][P:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[Cl:1][CH2:2][CH2:3][CH2:4][P:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | ClCCCCl.[Li][P](c1ccccc1)c1ccccc1 | ClCCCP(c1ccccc1)c1ccccc1 | null | null | O.O1CCCC1.C(C)OCC | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccc(Pc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[Li]-[P;H0;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[P;H0;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | null | [] | 0 | CELSIUS | 1 | HOUR | To a 500 mL round bottom flask there was added 400 mL of dry tetrahydrofuran followed by 0.081 mole of HPPh2. The mixture was cooled to 0° C. and 0.081 mole of n-butyl lithium was slowly added to generate LiPPh2 ; this was slowly warmed to room temperature and stirred for about one hour. The solution was transferred to... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1 | Li | O.O1CCCC1.C(C)OCC | 0 | 1 | ClCCCCl.[Li][P](c1ccccc1)c1ccccc1>O.O1CCCC1.C(C)OCC>ClCCCP(c1ccccc1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5aa13ac42e5f4ec7a4920f45b70632bb | COC(=O)[C@H](C)N.Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)O>>COC(=O)[C@@H](C)NC(=O)C(Cc1c(C)cc(O)cc1C)NC(=O)OC(C)(C)C | CN1CCOCC1.CN1CCOCC1.C(C)(C)(C)OC(=O)N[C@@H](CC1=C(C=C(C=C1C)O)C)C(=O)O.Cl.COC([C@@H](N)C)=O>>CC(C)(OC(=O)NC(CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)OC)C | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH3:6])[NH2:7].O[C:8](=[O:9])[C@H:10]([CH2:11][c:12]1[c:13]([CH3:14])[cH:15][c:16]([OH:17])[cH:18][c:19]1[CH3:20])[NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH3:6])[NH:7][C:8](=[O:9])[CH:10]([CH2:11][c:12]1[c:13]([CH3:14])[cH:15][... | COC(=O)[C@H](C)N.Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)O | COC(=O)[C@@H](C)NC(=O)C(Cc1c(C)cc(O)cc1C)NC(=O)OC(C)(C)C | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@@H;D3;+0:3](-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12]-[c:13].[C;D1;H3:14]-[#8:15]-[C:16](=[O;D1;H0:17])-[C:18](-[C;D1;H3:19])-[NH2;D1;+0:20]>>[C;D1;H3:14]-[#8:15]-[C:16](=[O;D1;H0:17])-[C:18](-[C;D1;H3:19])-[NH;D2;+0:20]-[C;H0;D3;+0:1](=... | 98.9 | [{"value": 98.9, "product": "CC(C)(OC(=O)NC(CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 16 | HOUR | Racemic t-butoxycarbonyl 2,6-dimethyltyrosine (3.9 g, 10 mmoles) was dissolved in 30 ml of CH2Cl2 by adding 1.12 ml (10 mmoles) of NMM. After bringing this mixture to reflux it was cooled to -30° C. and 1.32 ml (10 mmoles) of IBCF were added to this stirred solution. The temperature was allowed to rise to -15° C. and t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C(Cl)Cl | -30 | 16 | COC(=O)[C@H](C)N.Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)O>C(Cl)Cl>COC(=O)[C@@H](C)NC(=O)C(Cc1c(C)cc(O)cc1C)NC(=O)OC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-49bfa957cdb54d11874d4d10e9a37feb | COC(=O)[C@@H](C)NC(=O)C(Cc1c(C)cc(O)cc1C)NC(=O)OC(C)(C)C>>Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)O | CC(C)(OC(=O)NC(CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)OC)C>>CC(C)(OC(=O)N[C@@H](CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)O)C | C[O:27][C:25]([C@H:23]([NH:22][C:20]([CH:11]([CH2:10][c:9]1[c:2]([CH3:1])[cH:3][c:4]([OH:5])[cH:6][c:7]1[CH3:8])[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:21])[CH3:24])=[O:26]>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:6][c:7]([CH3:8])[c:9]1[CH2:10][C@H:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])... | COC(=O)[C@@H](C)NC(=O)C(Cc1c(C)cc(O)cc1C)NC(=O)OC(C)(C)C | Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)O | null | null | C(Cl)(Cl)Cl | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | The title compound was prepared by the methods of Example 9 using diastereomer F of the title compound of Example 6. [α]D -21.7 (CHCl3)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | C(Cl)(Cl)Cl | null | null | COC(=O)[C@@H](C)NC(=O)C(Cc1c(C)cc(O)cc1C)NC(=O)OC(C)(C)C>C(Cl)(Cl)Cl>Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7d46ffa09cc44e9392e4d49e8eb54422 | Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)O.NCCCc1ccccc1>>Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)NCCCc1ccccc1 | C1(=CC=CC=C1)CCCN.C(Cl)Cl.CC(C)(OC(=O)N[C@@H](CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)O)C.CN1CCOCC1>>CC(C)(OC(=O)N[C@@H](CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)NCCCC1=CC=CC=C1)C | O[C:25]([C@H:23]([NH:22][C:20]([C@H:11]([CH2:10][c:9]1[c:2]([CH3:1])[cH:3][c:4]([OH:5])[cH:6][c:7]1[CH3:8])[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:21])[CH3:24])=[O:26].[NH2:27][CH2:28][CH2:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:6][c:7]([CH3... | Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)O.NCCCc1ccccc1 | Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)NCCCc1ccccc1 | null | null | CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccccc1)NCC(=O)NCCCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | -45 | CELSIUS | 8 | HOUR | A CH2Cl2 solution (100 ml) of the title compound from Example 9, (16.6 g, 43.6 mmole) was charged with 4.4 g (43.6 mmoles) of NMM and cooled to -45° C. To this solution was added 5.7 g (43.6 mmole) of IBCF and the mixture warmed to 10° C. The solution was then cooled to -25° C. before adding 7.4 g (54.5 mmole) of 3-phe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CCOC(=O)C | -45 | 8 | Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)O.NCCCc1ccccc1>CCOC(=O)C>Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)NCCCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1397e52558304bc794ebf0497ed5c6b3 | Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N[C@H](C)C(=O)O>>Cc1cc(O)ccc1C[C@H](N)C(=O)N[C@H](C)C(=O)NCCCc1ccccc1 | Cl.CC1=C(C[C@H](N)C(=O)N[C@H](C)C(=O)O)C(=CC(=C1)O)C>>Cl.CC1=C(C[C@H](N)C(=O)N[C@H](C)C(=O)NCCCC2=CC=CC=C2)C=CC(=C1)O | O[C:17]([C@H:15]([NH:14][C:12]([C@H:10]([CH2:9][c:8]1[c:2]([CH3:1])[cH:3][c:4]([OH:5])[cH:6][c:7]1[CH3:20])[NH2:11])=[O:13])[CH3:16])=[O:18]>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:6][cH:7][c:8]1[CH2:9][C@H:10]([NH2:11])[C:12](=[O:13])[NH:14][C@H:15]([CH3:16])[C:17](=[O:18])[NH:19][CH2:20][CH2:21][CH2:22][c:23]1[cH:24][cH... | Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N[C@H](C)C(=O)O | Cc1cc(O)ccc1C[C@H](N)C(=O)N[C@H](C)C(=O)NCCCc1ccccc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | a8edcf7f55c2099e919c769dad8b38e5b55b77735d1757e3d7663e8e9f428c78 | 4b0f179f25479ea547f672763d671b032388c9c64c1dbabd2800d76835b4a424 | O=C(CCc1ccccc1)NCC(=O)NCCCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[c:9](:[c:10]):[c;H0;D3;+0:11](-[CH3;D1;+0:12]):[c:13]:[c:14]>>[C:15]-[C:16]-[CH2;D2;+0:12]-[#7:17]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:13]:[c:14] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 4 from diastereomer F of the title compound of Example 11, Route B. [α]D -23.8 (MeOH)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary amide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | CO | null | null | Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N[C@H](C)C(=O)O>CO>Cc1cc(O)ccc1C[C@H](N)C(=O)N[C@H](C)C(=O)NCCCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-adb591f5d8e14cf994f271977a5de703 | C=CCN1C(=O)c2ccccc2C1=O.Cc1cccc(C)c1Br>>Cc1cccc(C)c1C=CCN1C(=O)c2ccccc2C1=O | BrC1=C(C=CC=C1C)C.C(C=C)N1C(C=2C(C1=O)=CC=CC2)=O.C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>CC1=C(C(=CC=C1)C)C=CCN1C(C2=CC=CC=C2C1=O)=O | [CH2:9]=[CH:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22].Br[c:8]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1[CH3:7]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[CH:9]=[CH:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22] | C=CCN1C(=O)c2ccccc2C1=O.Cc1cccc(C)c1Br | Cc1cccc(C)c1C=CCN1C(=O)c2ccccc2C1=O | null | null | CCOCC.O.C(C)N(CC)CC | C-C Coupling | OtherReaction | 2d4a44695e29e4a9ab430c3b66736ad86dd99247e7216f16f3ca137abca78747 | df8442c9f2045421fb18548edb9c6acaeb9710f63e741d9f72e0000ca35c948a | O=C1c2ccccc2C(=O)N1CC=Cc1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](-[C;D1;H3:6]):[c:7].[C:8]-[C:9]=[CH2;D1;+0:10]>>[C:8]-[C:9]=[CH;D2;+0:10]-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](-[C;D1;H3:6]):[c:7] | null | [] | 100 | CELSIUS | null | null | A mixture 9.3 g (50 mmole) of 2-bromo-m-xylene, 15.0 g (80 mmole) of N-allylphthalimide, 0.56 (2.5 mmole) of paladium acetate and 1.44 (5.5 mmole) of triphenylphosphine were dissolved in 111 ml of triethylamine. The solution was placed in a sealed container and heated at 100° C. for 24 hours. The reaction was then dilu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Allyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HBr | CCOCC.O.C(C)N(CC)CC | 100 | null | C=CCN1C(=O)c2ccccc2C1=O.Cc1cccc(C)c1Br>CCOCC.O.C(C)N(CC)CC>Cc1cccc(C)c1C=CCN1C(=O)c2ccccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3ee8fe3c20534d3ebb7f9a94b9cce103 | Cc1cccc(C)c1C=CCN1C(=O)c2ccccc2C1=O>>Cc1cccc(C)c1CCCN1C(=O)c2ccccc2C1=O | CC1=C(C(=CC=C1)C)C=CCN1C(C2=CC=CC=C2C1=O)=O.CO>>CC1=C(C(=CC=C1)C)CCCN1C(C2=CC=CC=C2C1=O)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[CH:9]=[CH:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[CH2:9][CH2:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22] | Cc1cccc(C)c1C=CCN1C(=O)c2ccccc2C1=O | Cc1cccc(C)c1CCCN1C(=O)c2ccccc2C1=O | null | [Pd] | C1CCOC1 | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C1c2ccccc2C(=O)N1CCCc1ccccc1 | [O;D1;H0:1]=[C:2]-[#7:3](-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:10]=[O;D1;H0:11]>>[O;D1;H0:1]=[C:2]-[#7:3](-[C:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:10]=[O;D1;H0:11] | null | [] | null | null | 24 | HOUR | The title compound of Example 32 (10 g, 34 mmole) dissolved in 120 ml of THF and 100 ml of MeOH was reduced in a standard Parr hydrogenation apparatus using 1 g of 5% Pd/C as catalyst. The reaction was run at room temperature under a pressure of 5 psi for 24 hours. The residue after removing all solvent under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | null | [Pd].C1CCOC1 | null | 24 | Cc1cccc(C)c1C=CCN1C(=O)c2ccccc2C1=O>[Pd].C1CCOC1>Cc1cccc(C)c1CCCN1C(=O)c2ccccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-59ee8f90580b491d9685262ca4315869 | Cc1cccc(C)c1CCCN1C(=O)c2ccccc2C1=O>>Cc1cccc(C)c1CCCN | CC1=C(C(=CC=C1)C)CCCN1C(C2=CC=CC=C2C1=O)=O.C(C)O.NN>>CC1=C(C(=CC=C1)C)CCCN | O=C1c2ccccc2C(=O)[N:12]1[CH2:11][CH2:10][CH2:9][c:8]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1[CH3:7]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[CH2:9][CH2:10][CH2:11][NH2:12] | Cc1cccc(C)c1CCCN1C(=O)c2ccccc2C1=O | Cc1cccc(C)c1CCCN | null | null | null | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccccc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 59 | [{"value": 59.0, "product": "CC1=C(C(=CC=C1)C)CCCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 10 g (34.4 mmole) sample of the title compound of Example 33 was refluxed for 2 hours in 150 ml of ethanol containing 1.2 g (36.7 mmole) of 97% hydrazine. After concentrating the solution, the white crystalline residue was mixed with 100 ml of 10% NaOH and 100 ml of ether. The aqueous phase was separated and extracte... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1 | HO- | null | null | null | Cc1cccc(C)c1CCCN1C(=O)c2ccccc2C1=O>>Cc1cccc(C)c1CCCN |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-561ce089a1d34a40a3b38cb98f549b86 | O=Cc1ccccc1>>O=Cc1ccccc1 | C(C1=CC=CC=C1)=O.C(C=CC1=CC=CC=C1)=O>>C(C1=CC=CC=C1)=O.C(C=CC1=CC=CC=C1)=O | [O:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | O=Cc1ccccc1 | O=Cc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | FIG. 2 is the GC-IR spectrum for the bottoms in the distillation pot. The peak indicated by reference numeral 20 is the peak for benzaldehyde. The peak indicated by reference numeral 21 is the peak for the cinnamaldehyde.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | null | null | null | O=Cc1ccccc1>>O=Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-29e2e1d3d5724c9c82294db3f2de9b86 | Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](N)[C@H]2SC1.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>>Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(=O)/C(=N\OC3CCNC3=O)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)[C@H]2SC1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(NCC1)=O.N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O.ON1N=NC2=C1C=CC=C2.C1(CCCCC1)N=C=NC1CCCCC1>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)C2=... | [CH3:1][n:2]1[n:3][n:4][n:5][c:6]1[S:7][CH2:8][C:9]1=[C:10]([C:11](=[O:12])[O:13][CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[N:27]2[C:28](=[O:29])[C@@H:30]([NH2:31])[C@H:68]2[S:69][CH2:70]1.O[C:32](=[O:33])/[C:34](=[N:35]\[O:36][CH:37]1[CH2:38][CH2:39][NH:40][C:41]1=... | Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](N)[C@H]2SC1.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(=O)/C(=N\OC3CCNC3=O)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)[C@H]2SC1 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(OC(c1ccccc1)c1ccccc1)C1=C(CSc2nnn[nH]2)CS[C@@H]2[C@H](NC(=O)/C(=N\OC3CCNC3=O)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)C(=O)N12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3](=[#7:4]\[#8:5])-[c:6](:[#7;a:7]):[c:8]:[#16;a:9].[#16:10]-[C:11]1-[#7:12](-[C:13](-[C:14](-[#8:15])=[O;D1;H0:16])=[C:17])-[C:18](=[O;D1;H0:19])-[C:20]-1-[NH2;D1;+0:21]>>[#16:10]-[C:11]1-[#7:12](-[C:13](-[C:14](-[#8:15])=[O;D1;H0:16])=[C:17])-[C:18](=[O;D1;H0:19])-[C:20]-1-[NH;D2;+0:... | 59 | [{"value": 59.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O)=N/OC1C(NCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3.25 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid are dissolved in 200 ml of tetrahydrofuran, and 3.14 g of benzhydryl 7β-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylate, 1.03 g of 1-hydroxybenzotriazole and 1.57 g of dicyclohexylcarbodiimide are added thereto... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1nnn[nH]1.c1ccccc1.c1ccccc1.C1CCNC1.c1cscn1.c1ccccc1.c1ccccc1.c1ccccc1.C1=CN2CC[C@H]2SC1 | HO- | O1CCCC1 | null | 2 | Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](N)[C@H]2SC1.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>O1CCCC1>Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(=O)/C(=N\OC3CCNC3=O)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)[C@H]2SC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c50403bc6f784521a924357c892f597a | N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>>Nc1nc(/C(=N/OC2CCNC2=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(C[n+]4ccccc4)CS[C@H]23)cs1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(NCC1)=O.N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2=CC=CC=C2)C(=O)[O-])C1=O.C1(=C(C(=C(C(=C1F)F)F)N)F)N.Cl.Cl.C/C(=N\[Si](C)(C)C)/O[Si](C)(C)C.C(C(=O)Cl)(=O)Cl>>NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2=CC=CC=C2)C(=O)[O-])C1=O)=N/OC1C(NCC1)=O | [NH2:16][C@@H:17]1[C:18](=[O:19])[N:20]2[C:21]([C:22](=[O:23])[O-:24])=[C:25]([CH2:26][n+:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[CH2:33][S:34][C@H:35]12.O[C:14](/[C:5]([c:4]1[n:3][c:2]([NH:1]C(c2ccccc2)(c2ccccc2)c2ccccc2)[s:37][cH:36]1)=[N:6]\[O:7][CH:8]1[CH2:9][CH2:10][NH:11][C:12]1=[O:13])=[O:15]>>[NH2:1][c:2]1[n:... | N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | Nc1nc(/C(=N/OC2CCNC2=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(C[n+]4ccccc4)CS[C@H]23)cs1 | null | null | CN(C=O)C.C(Cl)(Cl)Cl.O.C(C)N(CC)CC | Acylation | OtherReaction | 781d8b3e409913340b6b1c61f41541a2f6dd66b9360c098a962238abbba4c82c | f20b37f950c024a98c8d203fe176865f0c41c478cf7e4a7e1363e3b299d98172 | O=C(N[C@@H]1C(=O)N2C=C(C[n+]3ccccc3)CS[C@H]12)/C(=N\OC1CCNC1=O)c1cscn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3](=[#7:4]\[#8:5])-[c:6]1:[#7;a:7]:[c:8](-[NH;D2;+0:9]-C(-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2):[#16;a:10]:[c:11]:1.[#16:12]-[C:13]1-[#7:14](-[C:15](=[O;D1;H0:16])-[C:17]-1-[NH2;D1;+0:18])-[C:19](-[C:20](-[O;-;D1;H0:21])=[O;D1;H0:22])=[C:23]>>[#16:12]-[C:13]1-[#7:14](-[C:15]... | null | [] | null | null | 15 | MINUTE | 0.57 g of oxalyl chloride is added at -5° to 0° C. to 15 ml of chloroform containing 0.35 g of dimethylformamide, and the mixture is stirred at the same temperature for 15 minutes. A mixture of 1.54 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid, 0.3 g of triethylamine and 15 ml of ch... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Secondary amine | Secondary amide.Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1cscn1.C1CCNC1.C1=CN2CC[C@H]2SC1.C1=CC=[NH+]C=C1 | HO- | CN(C=O)C.C(Cl)(Cl)Cl.O.C(C)N(CC)CC | null | 0.25 | N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>CN(C=O)C.C(Cl)(Cl)Cl.O.C(C)N(CC)CC>Nc1nc(/C(=N/OC2CCNC2=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(C[n+]4ccccc4)CS[C@H]23)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bf05a855f14647528c0f0fc05e736fca | N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>>Nc1nc(/C(=N/OC2CCNC2=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(C[n+]4ccccc4)CS[C@H]23)cs1 | N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2=CC=CC=C2)C(=O)[O-])C1=O.C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(NCC1)=O.C/C(=N\[Si](C)(C)C)/O[Si](C)(C)C.C1(=C(C(=C(C(=C1F)F)F)N)F)N.Cl.Cl.C(C(=O)Cl)(=O)Cl>>NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2=CC=CC=C2)C(=O)[O-])C1=O)=N/OC1C(NCC1)=O | [NH2:16][C@@H:17]1[C:18](=[O:19])[N:20]2[C:21]([C:22](=[O:23])[O-:24])=[C:25]([CH2:26][n+:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[CH2:33][S:34][C@H:35]12.O[C:14](/[C:5]([c:4]1[n:3][c:2]([NH:1]C(c2ccccc2)(c2ccccc2)c2ccccc2)[s:37][cH:36]1)=[N:6]\[O:7][CH:8]1[CH2:9][CH2:10][NH:11][C:12]1=[O:13])=[O:15]>>[NH2:1][c:2]1[n:... | N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | Nc1nc(/C(=N/OC2CCNC2=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(C[n+]4ccccc4)CS[C@H]23)cs1 | null | null | CN(C=O)C.C(Cl)(Cl)Cl.O.C(C)N(CC)CC | Acylation | OtherReaction | 781d8b3e409913340b6b1c61f41541a2f6dd66b9360c098a962238abbba4c82c | f20b37f950c024a98c8d203fe176865f0c41c478cf7e4a7e1363e3b299d98172 | O=C(N[C@@H]1C(=O)N2C=C(C[n+]3ccccc3)CS[C@H]12)/C(=N\OC1CCNC1=O)c1cscn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3](=[#7:4]\[#8:5])-[c:6]1:[#7;a:7]:[c:8](-[NH;D2;+0:9]-C(-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2):[#16;a:10]:[c:11]:1.[#16:12]-[C:13]1-[#7:14](-[C:15](=[O;D1;H0:16])-[C:17]-1-[NH2;D1;+0:18])-[C:19](-[C:20](-[O;-;D1;H0:21])=[O;D1;H0:22])=[C:23]>>[#16:12]-[C:13]1-[#7:14](-[C:15]... | null | [] | null | null | 15 | MINUTE | 1.56 g of oxalyl chloride are added at -5° to 0° C. to 39 ml of chloroform containing 0.99 ml of dimethylformamide, and the mixture is stirred at the same temperature for 15 minutes. A solution of 4.23 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid (d-isomer) and 0.84 g of triethylami... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Secondary amine | Secondary amide.Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1cscn1.C1CCNC1.C1=CN2CC[C@H]2SC1.C1=CC=[NH+]C=C1 | HO- | CN(C=O)C.C(Cl)(Cl)Cl.O.C(C)N(CC)CC | null | 0.25 | N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>CN(C=O)C.C(Cl)(Cl)Cl.O.C(C)N(CC)CC>Nc1nc(/C(=N/OC2CCNC2=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(C[n+]4ccccc4)CS[C@H]23)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-956934eb3d094e4c9e92a29f8cc49c84 | N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>>Nc1nc(/C(=N/OC2CCNC2=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(C[n+]4ccccc4)CS[C@H]23)cs1 | N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2=CC=CC=C2)C(=O)[O-])C1=O.C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(NCC1)=O.C/C(=N\[Si](C)(C)C)/O[Si](C)(C)C.C1(=C(C(=C(C(=C1F)F)F)N)F)N.Cl.Cl.C(C(=O)Cl)(=O)Cl>>NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2=CC=CC=C2)C(=O)[O-])C1=O)=N/OC1C(NCC1)=O | [NH2:16][C@@H:17]1[C:18](=[O:19])[N:20]2[C:21]([C:22](=[O:23])[O-:24])=[C:25]([CH2:26][n+:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[CH2:33][S:34][C@H:35]12.O[C:14](/[C:5]([c:4]1[n:3][c:2]([NH:1]C(c2ccccc2)(c2ccccc2)c2ccccc2)[s:37][cH:36]1)=[N:6]\[O:7][CH:8]1[CH2:9][CH2:10][NH:11][C:12]1=[O:13])=[O:15]>>[NH2:1][c:2]1[n:... | N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | Nc1nc(/C(=N/OC2CCNC2=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(C[n+]4ccccc4)CS[C@H]23)cs1 | null | null | CN(C=O)C.C(Cl)(Cl)Cl.O.C(C)N(CC)CC | Acylation | OtherReaction | 781d8b3e409913340b6b1c61f41541a2f6dd66b9360c098a962238abbba4c82c | f20b37f950c024a98c8d203fe176865f0c41c478cf7e4a7e1363e3b299d98172 | O=C(N[C@@H]1C(=O)N2C=C(C[n+]3ccccc3)CS[C@H]12)/C(=N\OC1CCNC1=O)c1cscn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3](=[#7:4]\[#8:5])-[c:6]1:[#7;a:7]:[c:8](-[NH;D2;+0:9]-C(-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2):[#16;a:10]:[c:11]:1.[#16:12]-[C:13]1-[#7:14](-[C:15](=[O;D1;H0:16])-[C:17]-1-[NH2;D1;+0:18])-[C:19](-[C:20](-[O;-;D1;H0:21])=[O;D1;H0:22])=[C:23]>>[#16:12]-[C:13]1-[#7:14](-[C:15]... | null | [] | null | null | 15 | MINUTE | 1.81 g of oxalyl chloride are added at -5° to 0° C. to 45 ml of chloroform containing 1.15 ml of dimethylformamide, and the mixture is stirred at the same temperature for 15 minutes. A solution of 4.90 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid (l-isomer) and 0.97 g of triethylami... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Secondary amine | Secondary amide.Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1cscn1.C1CCNC1.C1=CN2CC[C@H]2SC1.C1=CC=[NH+]C=C1 | HO- | CN(C=O)C.C(Cl)(Cl)Cl.O.C(C)N(CC)CC | null | 0.25 | N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12.O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>CN(C=O)C.C(Cl)(Cl)Cl.O.C(C)N(CC)CC>Nc1nc(/C(=N/OC2CCNC2=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(C[n+]4ccccc4)CS[C@H]23)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dcdecb3ff4504c268e9963b236d8ca55 | CN1CCC(O/N=C(\C(=O)O)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C1=O.Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](N)[C@H]2SC1>>CN1CCC(O/N=C(\C(=O)N[C@@H]2C(=O)N3C(C(=O)OC(c4ccccc4)c4ccccc4)=C(CSc4nnnn4C)CS[C@H]23)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C1=O | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(N(CC1)C)=O.N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O.ON1N=NC2=C1C=CC=C2.C1(CCCCC1)N=C=NC1CCCCC1>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)... | O[C:9](/[C:8](=[N:7]\[O:6][CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[C:70]1=[O:71])[c:45]1[cH:46][s:47][c:48]([NH:49][C:50]([c:51]2[cH:52][cH:53][cH:54][cH:55][cH:56]2)([c:57]2[cH:58][cH:59][cH:60][cH:61][cH:62]2)[c:63]2[cH:64][cH:65][cH:66][cH:67][cH:68]2)[n:69]1)=[O:10].[NH2:11][C@@H:12]1[C:13](=[O:14])[N:15]2[C:16]([C:17](... | CN1CCC(O/N=C(\C(=O)O)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C1=O.Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](N)[C@H]2SC1 | CN1CCC(O/N=C(\C(=O)N[C@@H]2C(=O)N3C(C(=O)OC(c4ccccc4)c4ccccc4)=C(CSc4nnnn4C)CS[C@H]23)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C1=O | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(OC(c1ccccc1)c1ccccc1)C1=C(CSc2nnn[nH]2)CS[C@@H]2[C@H](NC(=O)/C(=N\OC3CCNC3=O)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)C(=O)N12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3](=[#7:4]\[#8:5])-[c:6](:[#7;a:7]):[c:8]:[#16;a:9].[#16:10]-[C:11]1-[#7:12](-[C:13](=[O;D1;H0:14])-[C:15]-1-[NH2;D1;+0:16])-[C:17](-[C:18](-[#8:19])=[O;D1;H0:20])=[C:21]>>[#16:10]-[C:11]1-[#7:12](-[C:13](=[O;D1;H0:14])-[C:15]-1-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3](=[#7:4]\... | 55.6 | [{"value": 55.6, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O)=N/OC1C(N(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1.5 g of (Z)-2-(2-tritylaminothiazol-4yl)-2-[(1-methyl-2-pyrrolidon-3-yl)oxyimino]acetic acid are dissolved in 50 ml of tetrahydrofuran, and 1.4 g of benzhydryl 7β-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylate, 0.6 g of 1-hydroxybenzotriazole and 0.92 g of dicyclohexylcarbodiimide are added the... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1.c1nnn[nH]1.C1=CN2CC[C@H]2SC1.c1cscn1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 2 | CN1CCC(O/N=C(\C(=O)O)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C1=O.Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](N)[C@H]2SC1>O1CCCC1>CN1CCC(O/N=C(\C(=O)N[C@@H]2C(=O)N3C(C(=O)OC(c4ccccc4)c4ccccc4)=C(CSc4nnnn4C)CS[C@H]23)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a830c0378624496eadb696b60415d2c3 | CCOC(=O)/C(=N\O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.O=C1NCCC1Br>>CCOC(=O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | O.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/O.BrC1C(NCC1)=O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/OC1C(NCC1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6](=[N:7]\[OH:8])[c:15]1[cH:16][s:17][c:18]([NH:19][C:20]([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)([c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][cH:38]2)[n:39]1.Br[CH:9]1[CH2:10][CH2:11][NH:12][C:13]1=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6... | CCOC(=O)/C(=N\O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.O=C1NCCC1Br | CCOC(=O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 317eedb09d1c792890d47d514a35926bbc4daa99bfe57136559b667b95b04fd5 | 17b9e5d9dc3dddebe82873b428e215e82f0ae8a4833be65593459a08ce2dbc71 | O=C1NCCC1ON=Cc1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-1=[O;D1;H0:6].[#16;a:7]:[c:8]:[c:9](/[C:10](=[#7:11]/[OH;D1;+0:12])-[C:13](-[#8:14])=[O;D1;H0:15]):[#7;a:16]>>[#16;a:7]:[c:8]:[c:9](/[C:10](=[#7:11]/[O;H0;D2;+0:12]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-1=[O;D1;H0:6])-[C:13](-[#8:14])=[O;D1;H0:15]):[#7;a:16] | 85.7 | [{"value": 85.7, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/OC1C(NCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 15.8 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate are dissolved in 70 ml of dimethylsulfoxide, and 5.8 g of anhydrous potassium carbonate are added thereto. The mixture is stirred at room temperature for 20 minutes. 6.6 g of 3-bromo-2-pyrrolidone are added to said mixture, and the mixture is stirr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Oxime | null | C1CCNC1 | C1CCNC1 | C1CCNC1.c1cscn1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CS(=O)C | null | 0.333333 | CCOC(=O)/C(=N\O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.O=C1NCCC1Br>CS(=O)C>CCOC(=O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-af5206e6c1674815b192c0f7deab3abf | CCOC(=O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>>O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/OC1C(NCC1)=O.[OH-].[Na+]>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(NCC1)=O | CC[O:3][C:2](=[O:1])/[C:4](=[N:5]\[O:6][CH:7]1[CH2:8][CH2:9][NH:10][C:11]1=[O:12])[c:13]1[cH:14][s:15][c:16]([NH:17][C:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)([c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[n:37]1>>[O:1]=[C:2]([OH:3])/[C:4](=[N:5]\[O:6][CH:7]1[CH2:8][CH... | CCOC(=O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1NCCC1ON=Cc1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])\[C:4]=[#7:5]>>[#7:5]=[C:4]\[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 75.1 | [{"value": 75.1, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(NCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 16.0 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetate are added to a mixture of 160 ml of methanol and 30 ml of an aqueous 2N sodium hydroxide solution, and the mixture is refluxed for 30 minutes under heating. After cooling, crystalline precipitates are collected by filtration and wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCNC1.c1cscn1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | CO | null | null | CCOC(=O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>CO>O=C(O)/C(=N\OC1CCNC1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c1ad53f92a1a465b9cea596d9c8433a5 | CCOC(=O)/C(=N\O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.CN1CCC(Br)C1=O>>CCOC(=O)/C(=N\OC1CCN(C)C1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | O.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/O.CN1C(C(CC1)Br)=O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/OC1C(N(CC1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6](=[N:7]\[OH:8])[c:16]1[cH:17][s:18][c:19]([NH:20][C:21]([c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)([c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[n:40]1.Br[CH:9]1[CH2:10][CH2:11][N:12]([CH3:13])[C:14]1=[O:15]>>[CH3:1][CH2:2][O:3][C:4](=[O... | CCOC(=O)/C(=N\O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.CN1CCC(Br)C1=O | CCOC(=O)/C(=N\OC1CCN(C)C1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | f54144ece452cc9ef90c8d4f40dc02acdd537713d549f4c07da5ccec39a0bd23 | 17b9e5d9dc3dddebe82873b428e215e82f0ae8a4833be65593459a08ce2dbc71 | O=C1NCCC1ON=Cc1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[C;D1;H3:5])-[C:6]-1=[O;D1;H0:7].[#16;a:8]:[c:9]:[c:10](/[C:11](=[#7:12]/[OH;D1;+0:13])-[C:14](-[#8:15])=[O;D1;H0:16]):[#7;a:17]>>[#16;a:8]:[c:9]:[c:10](/[C:11](=[#7:12]/[O;H0;D2;+0:13]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[C;D1;H3:5])-[C:6]-1=[O;D1;H0:7])-[C:14](-[#8:15])=[O;D1;H0:16]... | 64.2 | [{"value": 64.2, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/OC1C(N(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 2.7 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate are dissolved in 12 ml of dimethylsulfoxide, and 1.0 g of anhydrous potassium carbonate is added thereto under nitrogen gas atmosphere. The mixture is stirred at room temperature for 10 minutes. 1.2 g of 1-methyl-3-bromo-2-pyrrolidone are added to t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Oxime | null | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1cscn1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CS(=O)C | null | 0.166667 | CCOC(=O)/C(=N\O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.CN1CCC(Br)C1=O>CS(=O)C>CCOC(=O)/C(=N\OC1CCN(C)C1=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3facba9af3ca4dc89a1396be78296749 | O=C(O)[C@@H](O)[C@H](O)C(=O)O>>O=C(O)C[C@H](O)C(=O)O | [C@H]([C@@H](C(=O)O)O)(C(=O)O)O>>C([C@@H](O)CC(=O)O)(=O)O | O[C@H:4]([C:2](=[O:1])[OH:3])[C@H:5]([OH:6])[C:7](=[O:8])[OH:9]>>[O:1]=[C:2]([OH:3])[CH2:4][C@H:5]([OH:6])[C:7](=[O:8])[OH:9] | O=C(O)[C@@H](O)[C@H](O)C(=O)O | O=C(O)C[C@H](O)C(=O)O | null | null | CO | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | null | O-[C@H;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[C:5](-[O;D1;H1:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[O;D1;H0:3]=[C:2](-[O;D1;H1:4])-[CH2;D2;+0:1]-[C:5](-[O;D1;H1:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | null | null | null | null | One of the intermediates, (S)-1-methyl-3-pyrrolidinol, was synthetized with retention of optical purity as shown in Chart IX starting with (S)-malic acid. The (S)-1-methyl-3-pyrrolidinol was shown to be dextrorotatory. As an alternative method of obtaining the resolved isomers of 1-methyl-3-pyrrolidinol, the racemic mi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | null | Other | CO | null | null | O=C(O)[C@@H](O)[C@H](O)C(=O)O>CO>O=C(O)C[C@H](O)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b0c0fc9ef6e847a68cadcb68fa16fa36 | CN1CCC(O)C1.NC(=O)c1ccccc1O>>CN1CCC(Oc2ccccc2C(N)=O)C1 | [NH2-].[Na+].CN1CC(CC1)O.C[O-].[Na+].C(C=1C(O)=CC=CC1)(=O)N.C=1(C(=CC=CC1)S(=O)(=O)Cl)C>>CN1CC(CC1)OC1=C(C(=O)N)C=CC=C1 | O[CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:16]1.[OH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13]([NH2:14])=[O:15]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]([NH2:14])=[O:15])[CH2:16]1 | CN1CCC(O)C1.NC(=O)c1ccccc1O | CN1CCC(Oc2ccccc2C(N)=O)C1 | null | null | CN(C=O)C.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 44b469410ea73be701b0efff512ad33f9e3763acd25fb255ddd7939c9cf1269d | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCNC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C;D1;H3:4])-[C:5]-[C:6]-1.[N;D1;H2:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[C;D1;H3:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-[C:8](-[N;D1;H2:7])=[O;D1;H0:9])-[C:6]-[C:5]-1 | null | [] | 70 | CELSIUS | 2.5 | HOUR | To 85.6 g (2.2 moles) of sodium amide in 1.5 liter of dry toluene was added 202 g (2 moles) of 1-methyl-3-pyrrolidinol so as not to exceed a temperature of 50° C. The mixture was then heated to 70° C. for 4.5 hours. The mixture was cooled and 381 g (2 moles) of o-toluenesulfonylchloride was added at a rapid drop while ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HO- | CN(C=O)C.C1(=CC=CC=C1)C | 70 | 2.5 | CN1CCC(O)C1.NC(=O)c1ccccc1O>CN(C=O)C.C1(=CC=CC=C1)C>CN1CCC(Oc2ccccc2C(N)=O)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8bc1bf72c6db4804aa9927d96d2d0b1c | CN1CCC(O)C1.O=C(O)c1cccnc1Cl>>CN1CCC(Oc2ncccc2C(=O)[O-])C1 | C(C)(=O)[O-].[Na+].CN1CC(CC1)O.[H-].[Na+].ClC1=C(C(=O)O)C=CC=N1>>CN1CC(CC1)OC1=NC=CC=C1C(=O)[O-].[Na+] | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([OH:6])[CH2:16]1.Cl[c:7]1[n:8][cH:9][cH:10][cH:11][c:12]1[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:6][c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13](=[O:14])[O-:15])[CH2:16]1 | CN1CCC(O)C1.O=C(O)c1cccnc1Cl | CN1CCC(Oc2ncccc2C(=O)[O-])C1 | null | null | CS(=O)C | Functional Group Interconversion | OtherReaction | 573c3c8886c76f2095afc82b06ef70e7d8fe65f8893d97368a94b4e921cf8529 | 7f2e55d61afc782af1f96328fe8bb733d85eb8b217d202347fa855aaaeb12032 | c1ccc(OC2CCNC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]):[c:8].[#7:9]-[C:10]-[C:11](-[OH;D1;+0:12])-[C:13]>>[#7:9]-[C:10]-[C:11](-[O;H0;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](-[O-;H0;D1:7])=[O;D1;H0:6]):[c:8])-[C:13] | null | [] | null | null | 10 | MINUTE | To a stirred suspension of 6.4 g (0.13 mole) of 50% sodium hydride (mineral oil) in 50 ml of dimethylsulfoxide was added dropwise 6.4 g (0.063 mole) of 1-methyl-3-pyrrolidinol. During addition, the temperature rose from 25° C. to 31° C. After 10 minutes, a solution of 10 g (0.063 mole) of 2-chloronicotinic acid in 50 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Secondary alcohol | Ether | c1ccncc1 | c1ccncc1 | C1CC[NH]C1.c1ccncc1 | HCl | CS(=O)C | null | 0.166667 | CN1CCC(O)C1.O=C(O)c1cccnc1Cl>CS(=O)C>CN1CCC(Oc2ncccc2C(=O)[O-])C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cb8859507f564718bbce4716cd124083 | CN1CCC(Br)C1.NC(=O)c1cc(Cl)ccc1O.NC(=O)c1ccccc1O>>CN1CCC(Oc2ccc(Cl)cc2C(N)=O)C1.CN1CCC(Oc2ccc(Cl)cc2C(N)=O)C1.O | BrC1CN(CC1)C.ClC1=CC=C(C(C(=O)N)=C1)O.[H-].[Na+].C(C=1C(O)=CC=CC1)(=O)N>>O.ClC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C.ClC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C | Br[CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:17]1.[OH:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]1[C:14]([NH2:15])=[O:16].[cH:18]1[cH:25][c:24]([OH:23])[c:30]([C:31]([NH2:32])=[O:33])[cH:29][cH:27]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:6][c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]2[C:14]([NH2:15])=[O:16])[CH2:17]... | CN1CCC(Br)C1.NC(=O)c1cc(Cl)ccc1O.NC(=O)c1ccccc1O | CN1CCC(Oc2ccc(Cl)cc2C(N)=O)C1.CN1CCC(Oc2ccc(Cl)cc2C(N)=O)C1.O | null | null | CN(C=O)C.O | Aromatic Heterocycle Formation | OtherReaction | 01b90862cba7fba60c84a18798f089b5127049a78a40950ed9f28fdd21c81fe5 | 74e0a2077a887e150582bccf28106f84aebd7243b3a5a6678934f2544b9ecf2f | c1ccc(OC2CCNC2)cc1.c1ccc(OC2CCNC2)cc1 | Br-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C;D1;H3:4])-[C:5]-[C:6]-1.[N;D1;H2:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[c:15]:1-[OH;D1;+0:16].[N;D1;H2:17]-[C:18](=[O;D1;H0:19])-[c:20]:[c:21](-[OH;D1;+0:22]):[c:23]>>[C;D1;H3:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:22]-[c:21](:[c:23]):[c:20... | 34.1 | [{"value": 23.0, "product": "O.ClC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C.ClC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.1, "product": "O.ClC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C.ClC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a cooled suspension of 2.4 g (0.41 mole) sodium hydride in 50 ml of dimethylformamide was added dropwise 17 g (0.1 mole) of 5-chlorosalicylamide dissolved in 50 ml of dimethylformamide at a rate such that the temperature did not exceed 20° C. After addition of the salicylamide was complete, 16.7 g (0.1 mole) of 3-br... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol.Aromatic alcohol | Aromatic halide.Ether.Ether.Tertiary amine | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | Br- | CN(C=O)C.O | null | null | CN1CCC(Br)C1.NC(=O)c1cc(Cl)ccc1O.NC(=O)c1ccccc1O>CN(C=O)C.O>CN1CCC(Oc2ccc(Cl)cc2C(N)=O)C1.CN1CCC(Oc2ccc(Cl)cc2C(N)=O)C1.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5bf0c62c0ba34c788309186cc279405a | CN1CCC(O)C1.NC(=O)c1ccc2ccccc2c1O>>CN1CCC(Oc2c(C(N)=O)ccc3ccccc23)C1 | CS(=O)(=O)Cl.CN1CC(CC1)O.C(C)N(CC)CC.[Na].OC1=C(C=CC2=CC=CC=C12)C(=O)N>>CN1CC(CC1)OC1=C(C=CC2=CC=CC=C12)C(=O)N | O[CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:20]1.[OH:6][c:7]1[c:8]([C:9]([NH2:10])=[O:11])[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:6][c:7]2[c:8]([C:9]([NH2:10])=[O:11])[cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[CH2:20]1 | CN1CCC(O)C1.NC(=O)c1ccc2ccccc2c1O | CN1CCC(Oc2c(C(N)=O)ccc3ccccc23)C1 | null | null | C1=CC=CC=C1.O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 44b469410ea73be701b0efff512ad33f9e3763acd25fb255ddd7939c9cf1269d | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc2c(OC3CCNC3)cccc2c1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C;D1;H3:4])-[C:5]-[C:6]-1.[N;D1;H2:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[C;D1;H3:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-[C:8](-[N;D1;H2:7])=[O;D1;H0:9])-[C:6]-[C:5]-1 | null | [] | 75 | CELSIUS | 15 | MINUTE | In another vessel, 79 g (0.69 mole) of methanesulfonylchloride was added dropwise to a solution of 69.7 g (0.69 mole) of 1-methyl-3-pyrrolidinol and 77 g (0.76 mole) of triethylamine in 500 ml of dry benzene while cooling with an ice bath. The mixture was stirred 15 minutes and filtered. The filter cake was washed with... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C1=CC=CC=C1.O | 75 | 0.25 | CN1CCC(O)C1.NC(=O)c1ccc2ccccc2c1O>C1=CC=CC=C1.O>CN1CCC(Oc2c(C(N)=O)ccc3ccccc23)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d8c0cc498d57496e9455a867931d8c90 | CN1CCC(S)C1.O=C(O)c1cccnc1Cl>>CN1CCC(Sc2ncccc2C(=O)O)C1 | ClC1=C(C(=O)O)C=CC=N1.CN1CC(CC1)S.[H-].[Na+]>>CN1CC(CC1)SC1=NC=CC=C1C(=O)O | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([SH:6])[CH2:16]1.Cl[c:7]1[n:8][cH:9][cH:10][cH:11][c:12]1[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([S:6][c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13](=[O:14])[OH:15])[CH2:16]1 | CN1CCC(S)C1.O=C(O)c1cccnc1Cl | CN1CCC(Sc2ncccc2C(=O)O)C1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 83e1471f87e837809a4e2fb3e1de305c0d7a6603480e04a86024c7cd55ed85fb | b7fe376f7aad2517725eef26ab981e4baa6c31c5f38fdf89e7c52a4a2c6cc1d2 | c1ccc(SC2CCNC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8].[#7:9]-[C:10]-[C:11](-[SH;D1;+0:12])-[C:13]>>[#7:9]-[C:10]-[C:11](-[S;H0;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8])-[C:13] | null | [] | 60 | CELSIUS | 8 | HOUR | To a stirred suspension of 80 g (2 mole) of 60% sodium hydride (in mineral oil) in 800 ml of dry dimethylformamide, all heated to 60° C. and using nitrogen gas flow was added dropwise, a solution of 157.0 g (1 mole) of 2-chloronicotinic acid and 117 g (1 mole) of 1-methyl-3-pyrrolidinethiol in 300 ml of dimethylformami... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aliphatic thiol | Monosulfide | c1ccncc1 | c1ccncc1 | C1CC[NH]C1.c1ccncc1 | HCl | CN(C=O)C | 60 | 8 | CN1CCC(S)C1.O=C(O)c1cccnc1Cl>CN(C=O)C>CN1CCC(Sc2ncccc2C(=O)O)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a745416737d6407f8a23a934d3424d3d | O=C(O)c1cccnc1Cl.OC1CN(C2CCCCC2)C1>>O=C([O-])c1cccnc1OC1CN(C2CCCCC2)C1 | C1(CCCCC1)N1CC(C1)O.ClC1=C(C(=O)O)C=CC=N1.[H-].[Na+]>>C1(CCCCC1)N1CC(C1)OC1=NC=CC=C1C(=O)[O-].[Na+] | Cl[c:9]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][cH:6][cH:7][n:8]1.[OH:10][CH:11]1[CH2:12][N:13]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:20]1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[O:10][CH:11]1[CH2:12][N:13]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:20]1 | O=C(O)c1cccnc1Cl.OC1CN(C2CCCCC2)C1 | O=C([O-])c1cccnc1OC1CN(C2CCCCC2)C1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 573c3c8886c76f2095afc82b06ef70e7d8fe65f8893d97368a94b4e921cf8529 | 7f2e55d61afc782af1f96328fe8bb733d85eb8b217d202347fa855aaaeb12032 | c1ccc(OC2CN(C3CCCCC3)C2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]):[c:8].[OH;D1;+0:9]-[C:10]1-[C:11]-[#7:12]-[C:13]-1>>[O-;H0;D1:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[C:10]1-[C:11]-[#7:12]-[C:13]-1):[#7;a:2]:[c:3] | 86 | [{"value": 86.0, "product": "C1(CCCCC1)N1CC(C1)OC1=NC=CC=C1C(=O)[O-].[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "C1(CCCCC1)N1CC(C1)OC1=NC=CC=C1C(=O)[O-].[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | A solution of 105 g (0.68 mole) of 1-cyclohexyl-3-azetidinol and 106 g (0.68 mole) of 2-chloronicotinic acid in 400 ml of dry dimethylformamide was added at a rapid drop to 52 g (1.35 mole) of 60% sodium hydride/mineral oil suspended in 400 ml of dry dimethylformamide at 60° C. Mild exothermic reaction was noted. After... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Secondary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.C1C[NH]C1.C1CCCCC1 | HCl | CN(C=O)C | 60 | 2 | O=C(O)c1cccnc1Cl.OC1CN(C2CCCCC2)C1>CN(C=O)C>O=C([O-])c1cccnc1OC1CN(C2CCCCC2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b3282ab649924efeb49346007aa7bf75 | Clc1ccc2ccccc2n1.O=C=O>>O=C(O)c1cc2ccccc2nc1Cl | C(C)(C)NC(C)C.C(CCC)[Li].CCCCCC.ClC1=NC2=CC=CC=C2C=C1.C(=O)=O>>ClC1=NC2=CC=CC=C2C=C1C(=O)O | [cH:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12][c:13]1[Cl:14].[O:1]=[C:2]=[O:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12][c:13]1[Cl:14] | Clc1ccc2ccccc2n1.O=C=O | O=C(O)c1cc2ccccc2nc1Cl | null | null | O1CCCC1 | Acylation | OtherReaction | 78ee4f870a2bb40b1759c2e4cd484e204c5b2b946629ed40af42c92cfb454773 | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1ccc2ncccc2c1 | [Cl;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[O;H0;D1;+0:10]>>[Cl;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:[c;H0;D3;+0:7]:1-[C;H0;D3;+0:9](=[O;D1;H0:8])-[OH;D1;+0:10] | 62 | [{"value": 62.0, "product": "ClC1=NC2=CC=CC=C2C=C1C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | -65 | CELSIUS | null | null | To a solution of 21.3 ml (0.15 mole) of diisopropyl amine in 300 ml of dry tetrahydrofuran under a continuous nitrogen blanket, at -70° C., was added 61.6 ml of 2.7M n-butyllithium in hexane (0.165 mole) while maintaining the temperature at -60° to -70° C. Subsequent to this addition, the temperature was maintained at ... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | null | O1CCCC1 | -65 | null | Clc1ccc2ccccc2n1.O=C=O>O1CCCC1>O=C(O)c1cc2ccccc2nc1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bbe4662ee3c84951be6a4e98c39cf4dd | Clc1cncc(Cl)c1.O=C=O>>O=C(O)c1c(Cl)cncc1Cl | C(=O)=O.C(C)(C)NC(C)C.C(CCC)[Li].ClC=1C=NC=C(C1)Cl>>ClC=1C=NC=C(C1C(=O)O)Cl | [cH:4]1[c:5]([Cl:6])[cH:7][n:8][cH:9][c:10]1[Cl:11].[O:1]=[C:2]=[O:3]>>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([Cl:6])[cH:7][n:8][cH:9][c:10]1[Cl:11] | Clc1cncc(Cl)c1.O=C=O | O=C(O)c1c(Cl)cncc1Cl | null | null | CCCCCC.O1CCCC1 | Acylation | OtherReaction | aa033d9bf3794a09c2037c20bc6de9e9f91edade53ff65b01042aec8736af92c | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1ccncc1 | [Cl;D1;H0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6](-[Cl;D1;H0:7]):[cH;D2;+0:8]:1.[O;D1;H0:9]=[C;H0;D2;+0:10]=[O;H0;D1;+0:11]>>[Cl;D1;H0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6](-[Cl;D1;H0:7]):[c;H0;D3;+0:8]:1-[C;H0;D3;+0:10](=[O;D1;H0:9])-[OH;D1;+0:11] | null | [] | -70 | CELSIUS | 0.5 | HOUR | To a solution of 4.96 ml (0.036 mole) of diisopropylamine in 200 ml of tetrahydrofuran at -65° C. under a nitrogen blanket was added dropwise 14.9 ml of 2.5M n-butyllithium in hexane while maintaining the above temperature. Twenty minutes subsequent to that addition, a solution 5.0 g (0.034 mole) of 3,5-dichloropyridin... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1ccncc1 | c1ccncc1 | c1ccncc1 | null | CCCCCC.O1CCCC1 | -70 | 0.5 | Clc1cncc(Cl)c1.O=C=O>CCCCCC.O1CCCC1>O=C(O)c1c(Cl)cncc1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d01d6df666e947e8b991d4358df01960 | COC(=O)c1ccc2cnccc2c1O.N>>NC(=O)c1ccc2cnccc2c1O | N.COC(=O)C=1C(=C2C=CN=CC2=CC1)O.N>>OC1=C2C=CN=CC2=CC=C1C(=O)N | CO[C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][n:9][cH:10][cH:11][c:12]2[c:13]1[OH:14].[NH3:1]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][n:9][cH:10][cH:11][c:12]2[c:13]1[OH:14] | COC(=O)c1ccc2cnccc2c1O.N | NC(=O)c1ccc2cnccc2c1O | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc2cnccc2c1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH3;D0;+0:6]>>[NH2;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 5-Hydroxy-6-isoquinolinecarboxylic acid methyl ester as reported by Dyke, S. F. et al., in Tetrahedron 1973, 29(6), 857-62, is reacted with excess ammonia in a steel bomb for 12-18 hr. The excess ammonia is allowed to evaporate and the residue is crystallized from a suitable solvent mix such as ethyl acetate-toluene to... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccc2cnccc2c1 | HO- | null | null | null | COC(=O)c1ccc2cnccc2c1O.N>>NC(=O)c1ccc2cnccc2c1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a902a7150ecd47d6a1975e8b2de5b2ae | Cc1ccc2ccc(C(=O)O)c(O)c2n1>>COC(=O)c1ccc2ccc(C)nc2c1O | OC=1C(=CC=C2C=CC(=NC12)C)C(=O)O.B(F)(F)F.C([O-])(O)=O.[Na+]>>COC(=O)C1=CC=C2C=CC(=NC2=C1O)C | [OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][c:11]([CH3:12])[n:13][c:14]2[c:15]1[OH:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][c:11]([CH3:12])[n:13][c:14]2[c:15]1[OH:16] | Cc1ccc2ccc(C(=O)O)c(O)c2n1 | COC(=O)c1ccc2ccc(C)nc2c1O | null | null | null | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccc2ncccc2c1 | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c:4]>>[C;D1;H3:5]-[O;H0;D2;+0:3]-[C:2](=[O;D1;H0:1])-[c:4] | null | [] | null | null | null | null | 8-Hydroxy-2-methyl-7-quinolinecarboxylic acid (as reported by Meek, W. H. et al., in J. Chem. Eng. Data 1969, 14(3), 388-91) is reacted with methanolic boron trifluoride solution for several hours. The resulting mixture is added to an aqueous solution of sodium bicarbonate to give finally a basic solution. The solution... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccc2ncccc2c1 | Other | null | null | null | Cc1ccc2ccc(C(=O)O)c(O)c2n1>>COC(=O)c1ccc2ccc(C)nc2c1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-abab3f08dfb7407e8adcdfc18a9a3ffd | COC(=O)c1ccc2ccc(C)nc2c1O.N>>Cc1ccc2ccc(C(N)=O)c(O)c2n1 | N.COC(=O)C1=CC=C2C=CC(=NC2=C1O)C.N>>OC=1C(=CC=C2C=CC(=NC12)C)C(=O)N | CO[C:9]([c:8]1[cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:15][c:14]2[c:12]1[OH:13])=[O:11].[NH3:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([C:9]([NH2:10])=[O:11])[c:12]([OH:13])[c:14]2[n:15]1 | COC(=O)c1ccc2ccc(C)nc2c1O.N | Cc1ccc2ccc(C(N)=O)c(O)c2n1 | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc2ncccc2c1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[NH3;D0;+0:8]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:8])=[O;D1;H0:2]):[c:4] | null | [] | null | null | null | null | 8-Hydroxy-2-methyl-7-quinolinecarboxylic acid methyl ester is reacted with excess ammonia in a steel bomb for 12-18 hr. The excess ammonia is allowed to evaporate and the residue is crystallized from a suitable solvent to give the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: to evaporate; t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccc2ncccc2c1 | HO- | null | null | null | COC(=O)c1ccc2ccc(C)nc2c1O.N>>Cc1ccc2ccc(C(N)=O)c(O)c2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c857701e44354b45bafe59192161b725 | O=C(O)c1c(O)ccc2ncccc12>>COC(=O)c1c(O)ccc2ncccc12 | OC1=C(C=2C=CC=NC2C=C1)C(=O)O.B(F)(F)F.C([O-])(O)=O.[Na+]>>COC(=O)C=1C=2C=CC=NC2C=CC1O | [OH:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][cH:14][c:15]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][cH:14][c:15]12 | O=C(O)c1c(O)ccc2ncccc12 | COC(=O)c1c(O)ccc2ncccc12 | null | null | null | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccc2ncccc2c1 | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c:4]>>[C;D1;H3:5]-[O;H0;D2;+0:3]-[C:2](=[O;D1;H0:1])-[c:4] | null | [] | null | null | null | null | 6-Hydroxy-5-quinolinecarboxylic acid [as reported by Da Re, P. et al. in Ann. Chem. (Rome) 1970, 60(3), 215-24 (C.A. 73, 25338m)] is reacted with methanolic boron trifluoride solution for several hours. The resulting mixture is added to an aqueous solution of sodium bicarbonate to give finally a basic solution. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccc2ncccc2c1 | Other | null | null | null | O=C(O)c1c(O)ccc2ncccc12>>COC(=O)c1c(O)ccc2ncccc12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8364f102cacd4f039922a83884184b50 | COC(=O)c1c(O)ccc2ncccc12.N>>NC(=O)c1c(O)ccc2ncccc12 | N.COC(=O)C=1C=2C=CC=NC2C=CC1O.N>>OC1=C(C=2C=CC=NC2C=C1)C(=O)N | CO[C:2](=[O:3])[c:4]1[c:5]([OH:6])[cH:7][cH:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]12.[NH3:1]>>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[cH:7][cH:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]12 | COC(=O)c1c(O)ccc2ncccc12.N | NC(=O)c1c(O)ccc2ncccc12 | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc2ncccc2c1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[NH3;D0;+0:8]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:8])=[O;D1;H0:2]):[c:4] | null | [] | null | null | null | null | 6-Hydroxy-5-quinolinecarboxylic acid methyl ester is reacted with excess ammonia in a steel bomb for 12-18 hr. The excess ammonia is allowed to evaporate and the residue is crystallized from a suitable solvent to give the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: to evaporate; the residu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccc2ncccc2c1 | HO- | null | null | null | COC(=O)c1c(O)ccc2ncccc12.N>>NC(=O)c1c(O)ccc2ncccc12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a272ef90d6fd48a2baa2dfdab2953f6f | COC(=O)c1ccc2cccnc2c1O.N>>NC(=O)c1ccc2cccnc2c1O | N.COC(=O)C1=CC=C2C=CC=NC2=C1O.N>>OC=1C(=CC=C2C=CC=NC12)C(=O)N | CO[C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[c:13]1[OH:14].[NH3:1]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[c:13]1[OH:14] | COC(=O)c1ccc2cccnc2c1O.N | NC(=O)c1ccc2cccnc2c1O | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc2ncccc2c1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[NH3;D0;+0:8]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:8])=[O;D1;H0:2]):[c:4] | null | [] | null | null | null | null | 8-Hydroxy-7-quinolinecarboxylic acid methyl ester [as reported by Eckstein, Z. et al. in Pol. J. Chem. 1979, 53(11), 2373-7 (C.A. 92, 215243s)] is reacted with excess ammonia in a steel bomb for 12-18 hr. The excess ammonia is allowed to evaporate and the residue is crystallized from a suitable solvent to give the titl... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccc2ncccc2c1 | HO- | null | null | null | COC(=O)c1ccc2cccnc2c1O.N>>NC(=O)c1ccc2cccnc2c1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b804369893e54bd59770ee9a23839cc6 | CN.O=C(O)C[C@H](O)C(=O)O>>CN1C(=O)C[C@H](O)C1=O | C([C@@H](O)CC(=O)O)(=O)O.CN>>O[C@@H]1C(N(C(C1)=O)C)=O | [CH3:1][NH2:2].O[C:3](=[O:4])[CH2:5][C@H:6]([OH:7])[C:8](O)=[O:9]>>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][C@H:6]([OH:7])[C:8]1=[O:9] | CN.O=C(O)C[C@H](O)C(=O)O | CN1C(=O)C[C@H](O)C1=O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | c87adbc4872314c499da8105023ac82c15f4a7000eff749dc6651a62a17f08b1 | b7eb222f11e89f2ccff57aab9a5106ae4173f0ba94ac518e1a9f3b22a378531d | O=C1CCC(=O)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[O;D1;H1:5])-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[C;D1;H3:8]-[NH2;D1;+0:9]>>[C;D1;H3:8]-[N;H0;D3;+0:9]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[O;D1;H1:5])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | null | null | null | null | To a stirred solution of 134 g (1 mole) of (S)-malic acid in 700 ml of toluene was added 97 ml of 40% aqueous methylamine. The temperature slowly rose to 50° C. After 0.5 hr the stirred mixture was heated to reflux and the water was collected in a Dean-Stark trap for 48 hours. A total of 93 ml of water was collected. T... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine | Substituted dicarboximide | null | C1CC[NH]C1 | C1CC[NH]C1 | HO- | C1(=CC=CC=C1)C | null | null | CN.O=C(O)C[C@H](O)C(=O)O>C1(=CC=CC=C1)C>CN1C(=O)C[C@H](O)C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1c2ca15851eb4519b4b2de95c0278d64 | O=C(O)c1cc(Br)cnc1O.O=S(Cl)Cl>>O=C(O)c1cc(Br)cnc1Cl | BrC=1C=NC(=C(C(=O)O)C1)O.S(=O)(Cl)Cl>>BrC=1C=C(C(=NC1)Cl)C(=O)O | O[c:10]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][c:6]([Br:7])[cH:8][n:9]1.O=S(Cl)[Cl:11]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][n:9][c:10]1[Cl:11] | O=C(O)c1cc(Br)cnc1O.O=S(Cl)Cl | O=C(O)c1cc(Br)cnc1Cl | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ab85b19a1f19bdb0596b983dc6471067aedf5e7b894e737e6d16cd077bd81b42 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccncc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9] | null | [] | null | null | null | null | To 15 g (0.069 mole) of 5-bromo-2-hydroxy nicotinic acid was added 75 ml of thionyl chloride and 3 ml of dimethylformamide. The mixture was heated to reflux for 30 minutes. After cooling, the excess thionyl chloride was removed by rotary evaporation and the residue poured into water (1 liter) with vigorous agitation. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | CN(C=O)C | null | null | O=C(O)c1cc(Br)cnc1O.O=S(Cl)Cl>CN(C=O)C>O=C(O)c1cc(Br)cnc1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f3db1044f1d24b8cbe93aa3f0f632b1b | BrBr.O=C(O)c1cccnc1O>>O=C(O)c1cc(Br)cnc1O | Br[O-].[Na+].BrBr.[OH-].[Na+].Cl.OC1=C(C(=O)O)C=CC=N1.[OH-].[Na+].Br[O-].[Na+]>>BrC=1C=C(C(=NC1)O)C(=O)O | Br[Br:7].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:8][n:9][c:10]1[OH:11]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][n:9][c:10]1[OH:11] | BrBr.O=C(O)c1cccnc1O | O=C(O)c1cc(Br)cnc1O | null | null | O | Functional Group Interconversion | Bromination | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | Br-[Br;H0;D1;+0:1].[O;D1;H0:2]=[C:3](-[O;D1;H1:4])-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[cH;D2;+0:9]:[c:10]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[c:10]:[c:5](-[C:3](=[O;D1;H0:2])-[O;D1;H1:4]):[c:6]:[#7;a:7]:[c:8]:1 | 63.5 | [{"value": 63.5, "product": "BrC=1C=C(C(=NC1)O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 10 g (0.07 mole) of 2-hydroxy-nicotinic acid in 16.8 g of 50% sodium hydroxide (0.21 mole) diluted with 25 ml of water was added 200 ml of sodium hypobromite solution prepared by adding 13.6 g (0.17 mole) of bromine to a solution of 20.16 g of 50% sodium hydroxide (0.25 mole) in 125 ml of water at 0° C... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | O | null | 24 | BrBr.O=C(O)c1cccnc1O>O>O=C(O)c1cc(Br)cnc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ade44fe67a2945baad793a7536771fc1 | CN1CCC(CS(=O)(=O)[O-])C1.NC(=O)c1cc([N+](=O)[O-])ccc1Cl>>CN1CCC(Oc2ccc([N+](=O)[O-])cc2C(N)=O)C1 | CN1CC(CC1)CS(=O)(=O)[O-].S(C)(=O)(=O)[O-].ClC1=C(C(=O)N)C=C(C=C1)[N+](=O)[O-].CN1CC(CC1)CS(=O)(=O)[O-].[H-].[Na+].[H-].[Na+]>>CN1CC(CC1)OC1=C(C(=O)N)C=C(C=C1)[N+](=O)[O-] | O=S(=O)(C[CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:19]1)[O-:6].Cl[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[C:16]([NH2:17])=[O:18]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:6][c:7]2[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]2[C:16]([NH2:17])=[O:18])[CH2:19]1 | CN1CCC(CS(=O)(=O)[O-])C1.NC(=O)c1cc([N+](=O)[O-])ccc1Cl | CN1CCC(Oc2ccc([N+](=O)[O-])cc2C(N)=O)C1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 439d911140614b99d4b0270213d2dd4bbc4a10d8d14603e62682d5b8fe95f5ea | c6d4374ac8a696f9ab980fdeb90e66ca3eeaeaef655a92a405538f38cf46f692 | c1ccc(OC2CCNC2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[c:8].O=S(=O)(-[O-;H0;D1:9])-C-[CH;D3;+0:10]1-[C:11]-[#7:12](-[C;D1;H3:13])-[C:14]-[C:15]-1>>[C;D1;H3:13]-[#7:12]1-[C:11]-[CH;D3;+0:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[c:8])-[C:15]-[C:14]-1 | 12 | [{"value": 12.0, "product": "CN1CC(CC1)OC1=C(C(=O)N)C=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a cooled suspension of sodium hydride (2.42 g of 60% content 0.06 mole) in 50 ml of dimethylformamide under nitrogen was added dropwise a solution of 10 g (0.055 mole) of 2-chloro-5-nitrobenzamide in 20 ml dimethylformamide. The suspension was stirred at room temperature for 1 hr and heated to 60° C. at which time 9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Sulfonic acid | Ether | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | HCl | CN(C=O)C | null | 1 | CN1CCC(CS(=O)(=O)[O-])C1.NC(=O)c1cc([N+](=O)[O-])ccc1Cl>CN(C=O)C>CN1CCC(Oc2ccc([N+](=O)[O-])cc2C(N)=O)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-997cc09958b640a1bde80518045ba4ee | CN1CCC(OS(C)(=O)=O)C1.NC(=O)c1cc(F)ccc1O>>CN1CCC(Oc2ccc(F)cc2C(N)=O)C1 | [H-].[Na+].FC=1C=CC(=C(C(=O)N)C1)O.CS(=O)(=O)OC1CN(CC1)C>>FC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C | CS(=O)(=O)O[CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:17]1.[OH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]1[C:14]([NH2:15])=[O:16]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:6][c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]2[C:14]([NH2:15])=[O:16])[CH2:17]1 | CN1CCC(OS(C)(=O)=O)C1.NC(=O)c1cc(F)ccc1O | CN1CCC(Oc2ccc(F)cc2C(N)=O)C1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4cd4e2ef4402daea1a0b7965dafdb4b00359862c567c9e06b889c2e49b6abe2e | b300ae9ac00448343b04f8595ac10c40ddc175401f75ad1a9cb423839305bb59 | c1ccc(OC2CCNC2)cc1 | C-S(=O)(=O)-O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C;D1;H3:4])-[C:5]-[C:6]-1.[N;D1;H2:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[C;D1;H3:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-[C:8](-[N;D1;H2:7])=[O;D1;H0:9])-[C:6]-[C:5]-1 | 42 | [{"value": 42.0, "product": "FC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a suspension of 0.44 g (60% in oil, 0.011 mole) of sodium hydride in 10 ml of dimethylformamide was added 1.55 g (0.01 mole) of 5-fluoro-2-hydroxybenzamide in 10 ml of dimethylformamide under nitrogen atmosphere at room temperature. The reaction mixture was heated to 60° C. and 1.80 g (0.01 mole) of 1-methyl-3-pyrro... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic alcohol | Ether | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | MsOH.HO- | CN(C=O)C | 60 | null | CN1CCC(OS(C)(=O)=O)C1.NC(=O)c1cc(F)ccc1O>CN(C=O)C>CN1CCC(Oc2ccc(F)cc2C(N)=O)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-435668a26a354206868b7fe31bf80b92 | CN1CCC(Oc2ccccc2C(N)=O)C1.Cl>>CN1CC(CCCl)Oc2ccccc2C1=O | Cl.[OH-].[Na+].CN1CC(CC1)OC1=C(C(=O)N)C=CC=C1>>ClCCC1OC2=C(C(N(C1)C)=O)C=CC=C2 | N[C:15]([c:14]1[c:9]([O:8][CH:4]2[CH2:3][N:2]([CH3:1])[CH2:6][CH2:5]2)[cH:10][cH:11][cH:12][cH:13]1)=[O:16].[ClH:7]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16] | CN1CCC(Oc2ccccc2C(N)=O)C1.Cl | CN1CC(CCCl)Oc2ccccc2C1=O | null | null | O | Acylation | OtherReaction | cb864e5df478d892e502caba9af2a6ef1f73e19f716eb33c67df2d58a7f12def | 92f5a12174e525b54b2c2f8873e5699366007dab21a88f20092a23357fd3b663 | O=C1NCCOc2ccccc21 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-1.[ClH;D0;+0:12]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-[Cl;H0;D1;+0:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To 54 g (1.35 mole) of sodium hydroxide in 800 ml of water was added 148 g (0.67 mole) of 2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide and the mixture brought to reflux for 18 hr. The pH was adjusted to 7 with hydrochloric acid and the solution filtered and concentrated. The residue was boiled with 400 ml of isopropanol a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Tertiary amine | Primary halide.Tertiary amide | C1CC[NH]C1 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | O | null | null | CN1CCC(Oc2ccccc2C(N)=O)C1.Cl>O>CN1CC(CCCl)Oc2ccccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cff393a1d9df4371b88ee0b282584eb9 | O=C(O)c1ccccc1OC1CCN(Cc2ccccc2)C1.O=S(Cl)Cl>>O=C1c2ccccc2OC(CCCl)CN1Cc1ccccc1 | C(C1=CC=CC=C1)N1CC(CC1)OC1=C(C(=O)O)C=CC=C1.S(=O)(Cl)Cl.C(C)N(CC)CC>>C(C1=CC=CC=C1)N1CC(OC2=C(C1=O)C=CC=C2)CCCl | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH:10]1[CH2:11][CH2:12][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:14]1.O=S(Cl)[Cl:13]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[O:9][CH:10]([CH2:11][CH2:12][Cl:13])[CH2:14][N:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=C(O)c1ccccc1OC1CCN(Cc2ccccc2)C1.O=S(Cl)Cl | O=C1c2ccccc2OC(CCCl)CN1Cc1ccccc1 | null | null | null | Acylation | OtherReaction | 04ab18d7b86ac41d547f1a7cc24bd254cd42e07805bd192d850a732fbf8e3594 | 480e1213f0b6ae6e64eb6b56f0bbf3a6616fa40d8d7548a0768841fd453e5729 | O=C1c2ccccc2OCCN1Cc1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]-[C:8]-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[CH2;D2;+0:13]-1>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:13]-[C:12]-[C:11]-[C:10]-[N;H0;D3;+0:9](-[C:8]-[c:7])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 15 | MINUTE | To 85.7 g (0.29 mole) of 2-[(1-benzyl-3-pyrrolidinyl)oxy]-benzoic acid was added 150 ml of thionyl chloride. The solution stood for 15 min and was then refluxed 30 min. and concentrated in vacuo. The residue was twice treated with 250 ml of chloroform and concentrated in vacuo. The residue was dissolved in 500 ml of ch... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Primary halide.Tertiary amide | C1CC[NH]C1 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | null | null | 0.25 | O=C(O)c1ccccc1OC1CCN(Cc2ccccc2)C1.O=S(Cl)Cl>>O=C1c2ccccc2OC(CCCl)CN1Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c645a85016454f99b612218797b734fd | CN1CCC(Oc2ncccc2C(=O)[O-])C1.ClC(Cl)(Cl)Cl>>CN1CC(CCCl)Oc2ncccc2C1=O | Cl.CN1CC(CC1)OC1=NC=CC=C1C(=O)[O-].[Na+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Cl)(Cl)(Cl)Cl>>Cl.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2 | [O-][C:15]([c:14]1[c:9]([O:8][CH:4]2[CH2:3][N:2]([CH3:1])[CH2:6][CH2:5]2)[n:10][cH:11][cH:12][cH:13]1)=[O:16].ClC(Cl)(Cl)[Cl:7]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16] | CN1CCC(Oc2ncccc2C(=O)[O-])C1.ClC(Cl)(Cl)Cl | CN1CC(CCCl)Oc2ncccc2C1=O | null | null | C(Cl)(Cl)Cl.C(C)O | Acylation | OtherReaction | 34de71827526778a78cc572135af6e5ce66bf4e9ffb544c5773eef67e62f48d3 | 5929549c823e536f9598bef60fbc0516c2bebaf6b6c4ab82e5ffc04c678caaab | O=C1NCCOc2ncccc21 | Cl-C(-Cl)(-Cl)-[Cl;H0;D1;+0:1].[C;D1;H3:2]-[N;H0;D3;+0:3]1-[C:4]-[C:5](-[#8:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](-[C;H0;D3;+0:11](-[O-])=[O;D1;H0:12]):[c:13])-[C:14]-[CH2;D2;+0:15]-1>>[C;D1;H3:2]-[N;H0;D3;+0:3]1-[C:4]-[C:5](-[C:14]-[CH2;D2;+0:15]-[Cl;H0;D1;+0:1])-[#8:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:13])-[C;H0;D3;+0:11... | null | [] | null | null | null | null | Hydrogen chloride gas was bubbled into a suspension of 150 g (0.61 mole) of sodium 2-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinecarboxylate in 1 liter of chloroform until a pH of 6 was reached. To the stirred mixture was added 350 g (1.34 mole) of triphenylphosphine and 350 g (2.3 mole) of carbon tetrachloride and the re... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Tertiary amine | Primary halide.Tertiary amide | C1CC[NH]C1 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | Other | C(Cl)(Cl)Cl.C(C)O | null | null | CN1CCC(Oc2ncccc2C(=O)[O-])C1.ClC(Cl)(Cl)Cl>C(Cl)(Cl)Cl.C(C)O>CN1CC(CCCl)Oc2ncccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c053b5e3777d41259742c324f8181dc6 | CN1CCC(Oc2cc(Cl)ccc2C(N)=O)C1.Cl>>CN1CC(CCCl)Oc2cc(Cl)ccc2C1=O | S(=O)(Cl)Cl.Cl.[OH-].[Na+].ClC1=CC(=C(C(=O)N)C=C1)OC1CN(CC1)C>>ClC1=CC2=C(C(N(CC(O2)CCCl)C)=O)C=C1 | N[C:16]([c:15]1[c:9]([O:8][CH:4]2[CH2:3][N:2]([CH3:1])[CH2:6][CH2:5]2)[cH:10][c:11]([Cl:12])[cH:13][cH:14]1)=[O:17].[ClH:7]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]2[C:16]1=[O:17] | CN1CCC(Oc2cc(Cl)ccc2C(N)=O)C1.Cl | CN1CC(CCCl)Oc2cc(Cl)ccc2C1=O | null | null | O.C(C)(=O)OCC | Acylation | OtherReaction | cb864e5df478d892e502caba9af2a6ef1f73e19f716eb33c67df2d58a7f12def | 92f5a12174e525b54b2c2f8873e5699366007dab21a88f20092a23357fd3b663 | O=C1NCCOc2ccccc21 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-1.[ClH;D0;+0:12]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-[Cl;H0;D1;+0:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 59 | [{"value": 59.0, "product": "ClC1=CC2=C(C(N(CC(O2)CCCl)C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.9, "product": "ClC1=CC2=C(C(N(CC(O2)CCCl)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 10.4 g (0.26 mole) of sodium hydroxide in 150 ml of water was added 32 g (0.13 mole) of 4-chloro-2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide and the mixture was heated at reflux for 24 hr. The reaction mixture was adjusted to pH 6 with concentrated hydrochloric acid and filtered and the filtrate concentr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Tertiary amine | Primary halide.Tertiary amide | C1CC[NH]C1 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | O.C(C)(=O)OCC | null | null | CN1CCC(Oc2cc(Cl)ccc2C(N)=O)C1.Cl>O.C(C)(=O)OCC>CN1CC(CCCl)Oc2cc(Cl)ccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-df7988810032401cab96c5b96767b633 | CN1CCC(Oc2ccc(Br)cc2C(N)=O)C1.Cl>>CN1CC(CCCl)Oc2ccc(Br)cc2C1=O | S(=O)(Cl)Cl.[OH-].[Na+].BrC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C.C(C)N(CC)CC.Cl>>BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=O)C1 | N[C:16]([c:15]1[c:9]([O:8][CH:4]2[CH2:3][N:2]([CH3:1])[CH2:6][CH2:5]2)[cH:10][cH:11][c:12]([Br:13])[cH:14]1)=[O:17].[ClH:7]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]2[C:16]1=[O:17] | CN1CCC(Oc2ccc(Br)cc2C(N)=O)C1.Cl | CN1CC(CCCl)Oc2ccc(Br)cc2C1=O | null | null | O | Acylation | OtherReaction | cb864e5df478d892e502caba9af2a6ef1f73e19f716eb33c67df2d58a7f12def | 92f5a12174e525b54b2c2f8873e5699366007dab21a88f20092a23357fd3b663 | O=C1NCCOc2ccccc21 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-1.[ClH;D0;+0:12]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-[Cl;H0;D1;+0:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 60.2 | [{"value": 60.0, "product": "BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.2, "product": "BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 1 | HOUR | To a solution of 9.6 g (0.24 mole) of sodium hydroxide in 200 ml of water was added 37 g (0.12 mole) of 5-bromo-2-[(1-methyl-3-pyrrolidinyl)oxy]-benzamide and the mixture was heated at reflux for 18 hr. The pH of the mixture was adjusted to 6.7 with concentrated hydrochloric acid solution. The solution was concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Tertiary amine | Primary halide.Tertiary amide | C1CC[NH]C1 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | O | 15 | 1 | CN1CCC(Oc2ccc(Br)cc2C(N)=O)C1.Cl>O>CN1CC(CCCl)Oc2ccc(Br)cc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2aa2b529cc9e41ec87acb8746e1f89c9 | COc1ccc(OC2CCN(C)C2)c(C(N)=O)c1.Cl>>COc1ccc2c(c1)C(=O)N(C)CC(CCCl)O2 | [OH-].[Na+].COC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C.C(C)N(CC)CC.Cl.S(=O)(Cl)Cl.Cl.[OH-].[Na+]>>ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)OC | N[C:9]([c:7]1[c:6]([O:18][CH:14]2[CH2:13][N:11]([CH3:12])[CH2:16][CH2:15]2)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1)=[O:10].[ClH:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[N:11]([CH3:12])[CH2:13][CH:14]([CH2:15][CH2:16][Cl:17])[O:18]2 | COc1ccc(OC2CCN(C)C2)c(C(N)=O)c1.Cl | COc1ccc2c(c1)C(=O)N(C)CC(CCCl)O2 | null | null | O | Acylation | OtherReaction | cb864e5df478d892e502caba9af2a6ef1f73e19f716eb33c67df2d58a7f12def | 92f5a12174e525b54b2c2f8873e5699366007dab21a88f20092a23357fd3b663 | O=C1NCCOc2ccccc21 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-1.[ClH;D0;+0:12]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-[Cl;H0;D1;+0:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 23.2 | [{"value": 23.0, "product": "ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.2, "product": "ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 19.2 g (0.48 mole) of sodium hydroxide in 500 ml of water was added 60 g (0.24 mole) of 5-methoxy-2-[(1-methyl-3-pyrrolidinyl)oxy]-benzamide and the mixture was heated at reflux for 24 hr. The reaction mixture was cooled and the pH adjusted to 6.8 with concentrated hydrochloric acid. The mixture was co... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Tertiary amine | Primary halide.Tertiary amide | C1CC[NH]C1 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | O | null | 1 | COc1ccc(OC2CCN(C)C2)c(C(N)=O)c1.Cl>O>COc1ccc2c(c1)C(=O)N(C)CC(CCCl)O2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8b003d3c47b34351abfb5f38c61627e5 | CN1CC(CCCl)Oc2ccccc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2ccccc2C1=S | P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.[S-2].[K+].[K+].ClCCC1OC2=C(C(N(C1)C)=O)C=CC=C2>>ClCCC1OC2=C(C(N(C1)C)=S)C=CC=C2 | O=[C:15]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:16])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[S:16] | CN1CC(CCCl)Oc2ccccc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2ccccc2C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 43ac2affde81267970c96bfb182f28e85d876733ab6e6103821469d8ecc8ebf9 | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2ccccc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:9])(-S-2)-S-3>>[#8:8]-[c:7]:[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:9])-[#7:2](-[C;D1;H3:3])-[C:4] | null | [] | null | null | null | null | A mixture of 18.5 g (0.0834 mole) of phosphorus pentasulfide and 18.5 g potassium sulfide was ground together and added to a solution of 100 g (0.417 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in dry toluene, the mixture refluxed 24 hr. and filtered. The filtrate was concentrated and par... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)C[NH]CCO2.S1P2SP3SP1SP(S2)S3 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | C1(=CC=CC=C1)C | null | null | CN1CC(CCCl)Oc2ccccc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2ccccc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6e0e6792bd184b57bc64b7b90119b242 | CN1CC(CCCl)Oc2ncccc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2ncccc2C1=S | Cl.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2 | O=[C:15]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:16])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[S:16] | CN1CC(CCCl)Oc2ncccc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2ncccc2C1=S | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 816a6edebc5f63ded7e13b08c00c5ed3d008d78e0a633be008bee89d24cf2686 | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2ncccc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7](:[#7;a:8]:[c:9])-[#8:10].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:11])(-S-2)-S-3>>[#8:10]-[c:7](:[#7;a:8]:[c:9]):[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:11])-[#7:2](-[C;D1;H3:3])-[C:4] | null | [] | null | null | null | null | To a solution of 59 g (0.25 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)one hydrochloride in 1500 ml of chloroform was added 41.5 g (0.19 mole) of phosphorus pentasulfide and the mixture was heated to reflux for 18 hr. The mixture was filtered and the filtrate was extracted with dilut... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1cnc2c(c1)C[NH]CCO2.S1P2SP3SP1SP(S2)S3 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | Other | C(Cl)(Cl)Cl | null | null | CN1CC(CCCl)Oc2ncccc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C(Cl)(Cl)Cl>CN1CC(CCCl)Oc2ncccc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b8c658f123854d16ae3bbcb4846c2600 | CN1CC(CCCl)Oc2cc3ccccc3cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2cc3ccccc3cc2C1=S | ClCCC1OC2=C(C(N(C1)C)=O)C=C1C=CC=CC1=C2.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.[S-2].[K+].[K+]>>ClCCC1OC2=C(C(N(C1)C)=S)C=C1C=CC=CC1=C2 | O=[C:19]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[cH:17][c:18]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:20])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[cH:17][c:18]2[C:19]1=[S:20] | CN1CC(CCCl)Oc2cc3ccccc3cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2cc3ccccc3cc2C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 1eb83fcd5217da399ee5559afc76959b0a672b869d20760af7ca5ba8a49566a7 | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2cc3ccccc3cc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:9])(-S-2)-S-3>>[#8:8]-[c:7]:[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:9])-[#7:2](-[C;D1;H3:3])-[C:4] | null | [] | null | null | null | null | To a solution of 16.6 g (0.06 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylnaphth[2,3-f][1,4]oxazepin-5(4H)-one in 150 ml of dry toluene was added a mixture of 8.6 g (0.045 mole) of phosphorus pentasulfide and 8.6 g of potassium sulfide which had been ground together. The reaction mixture was stirred and heated at re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2cc3c(cc2c1)C[NH]CCO3.S1P2SP3SP1SP(S2)S3 | c1ccc2cc3c(cc2c1)C[NH]CCO3 | c1ccc2cc3c(cc2c1)C[NH]CCO3 | Other | C1(=CC=CC=C1)C | null | null | CN1CC(CCCl)Oc2cc3ccccc3cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2cc3ccccc3cc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-88fc48739333487995ac8ade2e3f01a2 | CN1CC(CCCl)Oc2cc(Cl)ccc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2cc(Cl)ccc2C1=S | ClC1=CC2=C(C(N(CC(O2)CCCl)C)=O)C=C1.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.[S-2].[K+].[K+]>>ClC1=CC2=C(C(N(CC(O2)CCCl)C)=S)C=C1 | O=[C:16]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:17])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]2[C:16]1=[S:17] | CN1CC(CCCl)Oc2cc(Cl)ccc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2cc(Cl)ccc2C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 43ac2affde81267970c96bfb182f28e85d876733ab6e6103821469d8ecc8ebf9 | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2ccccc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:9])(-S-2)-S-3>>[#8:8]-[c:7]:[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:9])-[#7:2](-[C;D1;H3:3])-[C:4] | 73.2 | [{"value": 55.0, "product": "ClC1=CC2=C(C(N(CC(O2)CCCl)C)=S)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.2, "product": "ClC1=CC2=C(C(N(CC(O2)CCCl)C)=S)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 43 g (0.16 mole) of 8-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in 400 ml of dry toluene was added a mixture of 23 g (0.12 mole) of phosphorus pentasulfide and 23 g of potassium sulfide which had been ground together. The reaction mixture was stirred and heated at reflux ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)C[NH]CCO2.S1P2SP3SP1SP(S2)S3 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | C1(=CC=CC=C1)C | null | null | CN1CC(CCCl)Oc2cc(Cl)ccc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2cc(Cl)ccc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bf2c4a25c1be4e5398f1ee32fffc150d | CN1CC(CCCl)Oc2ccc(Br)cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2ccc(Br)cc2C1=S | BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=O)C1.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.[S-2].[K+].[K+]>>BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=S)C1 | O=[C:16]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:17])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]2[C:16]1=[S:17] | CN1CC(CCCl)Oc2ccc(Br)cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2ccc(Br)cc2C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 43ac2affde81267970c96bfb182f28e85d876733ab6e6103821469d8ecc8ebf9 | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2ccccc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:9])(-S-2)-S-3>>[#8:8]-[c:7]:[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:9])-[#7:2](-[C;D1;H3:3])-[C:4] | 72.6 | [{"value": 72.0, "product": "BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=S)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=S)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 11.0 g (0.035 mole) of 7-bromo-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in 150 ml of dry toluene was added a mixture of 13.4 g (0.07 mole) of phosphorus pentasulfide and 13.4 g of potassium sulfide which had been ground together. The reaction mixture was heated at reflux for 5 ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)C[NH]CCO2.S1P2SP3SP1SP(S2)S3 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | C1(=CC=CC=C1)C | null | null | CN1CC(CCCl)Oc2ccc(Br)cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2ccc(Br)cc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dbc1d0fc06cc4d08ac04f8d8f4685b9b | CN1CC(CCCl)Oc2c(ccc3ccccc23)C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2c(ccc3ccccc23)C1=S | P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.[S-2].[K+].[K+].ClCCC1OC2=C(C(N(C1)C)=O)C=CC1=CC=CC=C12>>ClCCC1OC2=C(C(N(C1)C)=S)C=CC1=CC=CC=C12 | O=[C:19]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[c:10]1[cH:11][cH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:20])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[c:10]([cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[C:19]1=[S:20] | CN1CC(CCCl)Oc2c(ccc3ccccc23)C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2c(ccc3ccccc23)C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 4f9bdc2466921bc2076c80e5ea2471371d474d3969b50466e61ceafbbbe1642d | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2c1ccc1ccccc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:9])(-S-2)-S-3>>[#8:8]-[c:7]:[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:9])-[#7:2](-[C;D1;H3:3])-[C:4] | 84.1 | [{"value": 84.0, "product": "ClCCC1OC2=C(C(N(C1)C)=S)C=CC1=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "ClCCC1OC2=C(C(N(C1)C)=S)C=CC1=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 9.55 g of phosphorus pentasulfide and 9.5 g of potassium sulfide were ground together and added to a solution of 20.2 g (0.07 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylnaphth[2,1-f][1,4]oxazepin-5(4H)-one in 200 ml of dry toluene. The mixture was stirred and heated at reflux for 7 hr. The hot reaction... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2c3c(ccc2c1)C[NH]CCO3.S1P2SP3SP1SP(S2)S3 | c1ccc2c3c(ccc2c1)C[NH]CCO3 | c1ccc2c3c(ccc2c1)C[NH]CCO3 | Other | C1(=CC=CC=C1)C | null | null | CN1CC(CCCl)Oc2c(ccc3ccccc23)C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2c(ccc3ccccc23)C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8c189722a6464305b05c5f2ecbd00eea | CN1CC(CCCl)Oc2ccc(Cl)cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2ccc(Cl)cc2C1=S | ClC=1C=CC2=C(C(N(CC(O2)CCCl)C)=O)C1.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.[S-2].[K+].[K+]>>ClC=1C=CC2=C(C(N(CC(O2)CCCl)C)=S)C1 | O=[C:16]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:17])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[C:16]1=[S:17] | CN1CC(CCCl)Oc2ccc(Cl)cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2ccc(Cl)cc2C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 43ac2affde81267970c96bfb182f28e85d876733ab6e6103821469d8ecc8ebf9 | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2ccccc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:9])(-S-2)-S-3>>[#8:8]-[c:7]:[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:9])-[#7:2](-[C;D1;H3:3])-[C:4] | 86.1 | [{"value": 68.0, "product": "ClC=1C=CC2=C(C(N(CC(O2)CCCl)C)=S)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.1, "product": "ClC=1C=CC2=C(C(N(CC(O2)CCCl)C)=S)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 20 g (0.07 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in 200 ml of toluene was added a mixture of 9.55 g (0.05 mole) of phosphorus pentasulfide and 9.5 g of potassium sulfide which had been ground together. The reaction mixture was filtered and the filtrate conc... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)C[NH]CCO2.S1P2SP3SP1SP(S2)S3 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | C1(=CC=CC=C1)C | null | null | CN1CC(CCCl)Oc2ccc(Cl)cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2ccc(Cl)cc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ffbaf1c2ea5949e094d1b0c62e55de55 | COc1ccc2c(c1)C(=O)N(C)CC(CCCl)O2.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>COc1ccc2c(c1)C(=S)N(C)CC(CCCl)O2 | ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)OC.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.[S-2].[K+].[K+]>>ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)OC | O=[C:9]1[c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[O:18][CH:14]([CH2:15][CH2:16][Cl:17])[CH2:13][N:11]1[CH3:12].S=P12SP3(=S)SP(=S)(S1)SP(=[S:10])(S2)S3>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[S:10])[N:11]([CH3:12])[CH2:13][CH:14]([CH2:15][CH2:16][Cl:17])[O:18]2 | COc1ccc2c(c1)C(=O)N(C)CC(CCCl)O2.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | COc1ccc2c(c1)C(=S)N(C)CC(CCCl)O2 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 43ac2affde81267970c96bfb182f28e85d876733ab6e6103821469d8ecc8ebf9 | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2ccccc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:9])(-S-2)-S-3>>[#8:8]-[c:7]:[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:9])-[#7:2](-[C;D1;H3:3])-[C:4] | 86.3 | [{"value": 65.0, "product": "ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.3, "product": "ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 10.3 g (0.04 mole) of 2-(2-chloroethyl)-2,3-dihydro-7-methoxy-4-methyl-1,4-benzoxazepin-5(4H)-one in 200 ml of chloroform was added a mixture of 5.7 g (0.03 mole) of phosphorus pentasulfide and 5.7 g of potassium sulfide which had been ground together. The reaction mixture was stirred and heated at ref... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)C[NH]CCO2.S1P2SP3SP1SP(S2)S3 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | C(Cl)(Cl)Cl | null | null | COc1ccc2c(c1)C(=O)N(C)CC(CCCl)O2.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C(Cl)(Cl)Cl>COc1ccc2c(c1)C(=S)N(C)CC(CCCl)O2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3255470380604e3ea543506a53fd60a0 | CN1CCC(Sc2ncccc2C(=O)O)C1.ClC(Cl)Cl>>CN1CC(CCCl)Sc2ncccc2C1=O | CN1CC(CC1)SC1=NC=CC=C1C(=O)O.C(Cl)(Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>ClCCC1SC2=C(C(N(C1)C)=O)C=CC=N2 | O[C:15]([c:14]1[c:9]([S:8][CH:4]2[CH2:3][N:2]([CH3:1])[CH2:6][CH2:5]2)[n:10][cH:11][cH:12][cH:13]1)=[O:16].ClC(Cl)[Cl:7]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[S:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16] | CN1CCC(Sc2ncccc2C(=O)O)C1.ClC(Cl)Cl | CN1CC(CCCl)Sc2ncccc2C1=O | null | null | C(Cl)(Cl)(Cl)Cl | Acylation | OtherReaction | b95719b87574728c235c5497a52281e1c88156104d975f0a6e21c1cff9b129f8 | b49eb23b5b6ae322cfab26d1040968fb1a3018654a4d628d6b2e1582e31b01dc | O=C1NCCSc2ncccc21 | Cl-C(-Cl)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6](-[#16:7]-[C:8]1-[C:9]-[N;H0;D3;+0:10](-[C;D1;H3:11])-[CH2;D2;+0:12]-[C:13]-1):[#7;a:14]:[c:15]>>[C;D1;H3:11]-[N;H0;D3;+0:10]1-[C:9]-[C:8](-[C:13]-[CH2;D2;+0:12]-[Cl;H0;D1;+0:1])-[#16:7]-[c:6](:[#7;a:14]:[c:15]):[c:4](:[c:5])-[C;H0;D3;+0:2]-1=[... | null | [] | null | null | null | null | A mixture of 80.75 g (0.34 mole) of 2-[(1-methyl-3-pyrrolidinyl)thio]-3-pyridinecarboxylic acid, 500 ml of chloroform, 200 g of carbon tetrachloride and 178 g (0.68 mole) of triphenylphosphine was stirred at reflux for 2.5 hr. The resulting solution was extracted with one 500 ml and three 125 ml portions of 1N hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Carboxylic acid.Tertiary amine | Primary halide.Tertiary amide | C1CC[NH]C1 | c1cnc2c(c1)C[NH]CCS2 | c1cnc2c(c1)C[NH]CCS2 | HCl | C(Cl)(Cl)(Cl)Cl | null | null | CN1CCC(Sc2ncccc2C(=O)O)C1.ClC(Cl)Cl>C(Cl)(Cl)(Cl)Cl>CN1CC(CCCl)Sc2ncccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2835159553ab4fcdb331894bd71cc090 | CN1CC(CCCl)Sc2ncccc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CN1CC(CCCl)Sc2ncccc2C1=S | ClCCC1SC2=C(C(N(C1)C)=O)C=CC=N2.COC1=CC=C(C=C1)P1(SP(S1)(C1=CC=C(C=C1)OC)=S)=S>>ClCCC1SC2=C(C(N(C1)C)=S)C=CC=N2 | O=[C:15]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[S:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]21.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:16])S2)cc1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[S:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[S:16] | CN1CC(CCCl)Sc2ncccc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CN1CC(CCCl)Sc2ncccc2C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | a9e26ac969be1f2f1da5297fa4500a483fb9a743fb354b404df74b4cf1e3597f | 6bfe9cf75b76e7dc07d0e23f56b0121cbe043c2e701d72c5be7acc1ccd1adcd8 | S=C1NCCSc2ncccc21 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3](-[C;D1;H3:4])-[C:5])-[c:6](:[c:7]):[c:8](:[#7;a:9]:[c:10])-[#16:11]>>[#16:11]-[c:8](:[#7;a:9]:[c:10]):[c:6](:[c:7])-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3](-[C;D1;H3:4])-[C:5] | null | [] | null | null | null | null | A mixture of 4.3 g (0.017 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]thiazepin-5(4H)-one, 100 ml of toluene and 4.8 g (0.012 mole) of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide was refluxed for 3 hr and then extracted twice with dilute sodium hydroxide. The organic layer wa... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide.Monosulfide.Monosulfide | Thioamide | c1cnc2c(c1)C[NH]CCS2.c1ccccc1.P1SPS1.c1ccccc1 | c1cnc2c(c1)C[NH]CCS2 | c1cnc2c(c1)C[NH]CCS2 | Other | C1(=CC=CC=C1)C | null | null | CN1CC(CCCl)Sc2ncccc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1(=CC=CC=C1)C>CN1CC(CCCl)Sc2ncccc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2f0a54101bda4c5984ec97659afe8d34 | CN1CC(CCCl)Oc2ccncc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CN1CC(CCCl)Oc2ccncc2C1=S.Cl | ClCCC1OC2=C(C(N(C1)C)=O)C=NC=C2.COC1=CC=C(C=C1)P2(=S)SP(=S)(S2)C3=CC=C(C=C3)OC>>Cl.ClCCC1OC2=C(C(N(C1)C)=S)C=NC=C2 | O=[C:15]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][n:12][cH:13][c:14]21.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:16])S2)cc1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][n:12][cH:13][c:14]2[C:15]1=[S:16].[ClH:17] | CN1CC(CCCl)Oc2ccncc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CN1CC(CCCl)Oc2ccncc2C1=S.Cl | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 04ec00afe311ae1bac323818e55a61a601447b5418e04284e19e06cf3a0fa74b | 6bfe9cf75b76e7dc07d0e23f56b0121cbe043c2e701d72c5be7acc1ccd1adcd8 | S=C1NCCOc2ccncc21 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3](-[C;D1;H3:4])-[C:5])-[c:6](:[c:7]:[#7;a:8]:[c:9]):[c:10]-[#8:11]>>[#8:11]-[c:10]:[c:6](:[c:7]:[#7;a:8]:[c:9])-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3](-[C;D1;H3:4])-[C:5] | null | [] | null | null | null | null | 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,4-f][1,4]oxazepin-5(4H)-one, 15 g (0.06 mole), was dissolved in 200 ml of dry toluene and 15 g (0.037 mole) of [2,4-bis (4-methoxyphenyl)-1,3,2,4-dithiaphosphetane-2,4-disulfide was added. The mixture was refluxed for 2.5 hr and the toluene solution decanted. The residue w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide.Monosulfide.Monosulfide | Thioamide | c1cc2c(cn1)C[NH]CCO2.c1ccccc1.P1SPS1.c1ccccc1 | c1cc2c(cn1)C[NH]CCO2 | c1cc2c(cn1)C[NH]CCO2 | Other | C1(=CC=CC=C1)C | null | null | CN1CC(CCCl)Oc2ccncc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2ccncc2C1=S.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-11860a3dcb584788ab48608c74e8cc2e | CN1CC(CCCl)Oc2ncccc2C1=O.Cl>>CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O | Cl.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.S(=O)(=O)(Cl)Cl>>ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=O | [CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[n:10][cH:11][cH:12][cH:14][c:15]2[C:16]1=[O:17].[ClH:13]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[n:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[C:16]1=[O:17] | CN1CC(CCCl)Oc2ncccc2C1=O.Cl | CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O | null | null | CN(C=O)C | Functional Group Addition | Chlorination | ad372abf1019cea33b6a7dcea0ff6c8338a6fd5f614d94a79ff142e83977e890 | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | O=C1NCCOc2ncccc21 | [#7:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[c:7]:[#7;a:8]:[c:9]:1-[#8:10].[ClH;D0;+0:11]>>[#7:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:11]):[c:7]:[#7;a:8]:[c:9]:1-[#8:10] | 6.4 | [{"value": 6.4, "product": "ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A sample of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5-(4H)-one hydrochloride (10 g, 136 mole) was dissolved in dimethylformamide (150 ml) and heated to reflux. Sulfuryl chloride (20 g, 0.148 mole) was then added dropwise over a period of 40-50 minutes. The reaction was allowed to stir at reflu... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | null | CN(C=O)C | null | null | CN1CC(CCCl)Oc2ncccc2C1=O.Cl>CN(C=O)C>CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d509aa5423c6487cbbe6785e60b235b3 | CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CN1CC(CCCl)Oc2ncc(Cl)cc2C1=S | ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=O.COC1=CC=C(C=C1)P1(SP(S1)(C1=CC=C(C=C1)OC)=S)=S>>ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=S | O=[C:16]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[n:10][cH:11][c:12]([Cl:13])[cH:14][c:15]21.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:17])S2)cc1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[n:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[C:16]1=[S:17] | CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CN1CC(CCCl)Oc2ncc(Cl)cc2C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 0a918a3e4aff4213dc84ed5746fe3e4f2528e6cf920242bc5ada6cfd1a73c2d5 | 6bfe9cf75b76e7dc07d0e23f56b0121cbe043c2e701d72c5be7acc1ccd1adcd8 | S=C1NCCOc2ncccc21 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3](-[C;D1;H3:4])-[C:5])-[c:6](:[c:7]):[c:8](:[#7;a:9]:[c:10])-[#8:11]>>[#8:11]-[c:8](:[#7;a:9]:[c:10]):[c:6](:[c:7])-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3](-[C;D1;H3:4])-[C:5] | null | [] | null | null | 2 | HOUR | 7-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido [3,2-f][1,4]oxazepin-5(4H)-one, 6.0 g (0.022 mole) was suspended in 200 ml of toluene. To this suspension was added 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-dilsulfide. The mixture was heated to reflux with vigorous stirring for 2 hours. Because the... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide.Monosulfide.Monosulfide | Thioamide | c1cnc2c(c1)C[NH]CCO2.c1ccccc1.P1SPS1.c1ccccc1 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | Other | C1(=CC=CC=C1)C | null | 2 | CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2ncc(Cl)cc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-29596a0f7ab14275afad8e96b1c3628f | CN1CC(CCCl)Oc2ncccc2C1=O.O=C1NC(=O)c2ccccc21>>CN1CC(CCN2C(=O)c3ccccc3C2=O)Oc2ncccc2C1=O | ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K]>>O=C1N(C(C2=CC=CC=C12)=O)CCC1OC2=C(C(N(C1)C)=O)C=CC=N2 | Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:25](=[O:26])[c:24]2[c:19]([n:20][cH:21][cH:22][cH:23]2)[O:18]1.[NH:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]1=[O:17]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C:16]2=[O:17])[O:18][c:19]2[n... | CN1CC(CCCl)Oc2ncccc2C1=O.O=C1NC(=O)c2ccccc21 | CN1CC(CCN2C(=O)c3ccccc3C2=O)Oc2ncccc2C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2022cc53c1563230994721760c16c873bbdd2982bbfbeeef5b40885f32de1173 | ed5b40ca5c14bda1cdc43d7e7526ae39e9e787b52b58ca2afd56239c19d62539 | O=C1NCC(CCN2C(=O)c3ccccc3C2=O)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]-1>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6](=[O;D1;H0:5])-[c:11]:[c:10]-[C:8]-1=[O;D1;H0:9] | 37 | [{"value": 36.0, "product": "O=C1N(C(C2=CC=CC=C12)=O)CCC1OC2=C(C(N(C1)C)=O)C=CC=N2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.0, "product": "O=C1N(C(C2=CC=CC=C12)=O)CCC1OC2=C(C(N(C1)C)=O)C=CC=N2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | To a solution of 4.92 g (0.02 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepin-5-(4H)one in 35 ml of dimethylformamide was added 7.55 g (0.041 mole) of potassium phthalimide. The mixture was stirred for 5 hr at 100° C. and left standing at room temperature overnight. Dimethylformamide was remov... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1cnc2c(c1)C[NH]CCO2 | HCl | CN(C=O)C | 100 | 5 | CN1CC(CCCl)Oc2ncccc2C1=O.O=C1NC(=O)c2ccccc21>CN(C=O)C>CN1CC(CCN2C(=O)c3ccccc3C2=O)Oc2ncccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-83c82ca7cc2843bba7adbd8cf14ed2fd | CN1CC(CCC#N)Oc2ncccc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CN1CC(CCC#N)Oc2ncccc2C1=S | COC1=CC=C(C=C1)P1(SP(S1)(C1=CC=C(C=C1)OC)=S)=S.CN1CC(OC2=C(C1=O)C=CC=N2)CCC#N.COC1=CC=C(C=C1)P1(SP(S1)(C1=CC=C(C=C1)OC)=S)=S>>CN1CC(OC2=C(C1=S)C=CC=N2)CCC#N | O=[C:16]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][C:7]#[N:8])[O:9][c:10]2[n:11][cH:12][cH:13][cH:14][c:15]21.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:17])S2)cc1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][C:7]#[N:8])[O:9][c:10]2[n:11][cH:12][cH:13][cH:14][c:15]2[C:16]1=[S:17] | CN1CC(CCC#N)Oc2ncccc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CN1CC(CCC#N)Oc2ncccc2C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 0a918a3e4aff4213dc84ed5746fe3e4f2528e6cf920242bc5ada6cfd1a73c2d5 | 6bfe9cf75b76e7dc07d0e23f56b0121cbe043c2e701d72c5be7acc1ccd1adcd8 | S=C1NCCOc2ncccc21 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3](-[C;D1;H3:4])-[C:5])-[c:6](:[c:7]):[c:8](:[#7;a:9]:[c:10])-[#8:11]>>[#8:11]-[c:8](:[#7;a:9]:[c:10]):[c:6](:[c:7])-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3](-[C;D1;H3:4])-[C:5] | 24.9 | [{"value": 13.8, "product": "CN1CC(OC2=C(C1=S)C=CC=N2)CCC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.9, "product": "CN1CC(OC2=C(C1=S)C=CC=N2)CCC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 11.0 g (0.04 mole) of 2,3,4,5-tetrahydro-4-methyl-5-oxopyrido[3,2-f][1,4]-oxazepine-2-propanenitrile in 175 ml toluene was added 10.5 g (0.026 mole) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide. The reaction mixture was heated to reflux for 2 hr with vigorous mechanical stirri... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide.Monosulfide.Monosulfide | Thioamide | c1cnc2c(c1)C[NH]CCO2.c1ccccc1.P1SPS1.c1ccccc1 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | Other | C1(=CC=CC=C1)C | null | 1 | CN1CC(CCC#N)Oc2ncccc2C1=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1(=CC=CC=C1)C>CN1CC(CCC#N)Oc2ncccc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-697c078422cb40a2878f7893b80f69c2 | CN1CCC(C)(O)C1.O=C(O)c1cccnc1Cl>>CN1CC(C)(CCCl)Oc2ncccc2C1=O.Cl | [H-].[Na+].O1CCCC1.CN(C=O)C.ClC1=C(C(=O)O)C=CC=N1.CN1CC(CC1)(O)C>>Cl.ClCCC1(OC2=C(C(N(C1)C)=O)C=CC=N2)C | [CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([OH:9])[CH2:6][CH2:7]1.O[C:16]([c:15]1[c:10]([Cl:8])[n:11][cH:12][cH:13][cH:14]1)=[O:17]>>[CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([CH2:6][CH2:7][Cl:8])[O:9][c:10]2[n:11][cH:12][cH:13][cH:14][c:15]2[C:16]1=[O:17].[ClH:18] | CN1CCC(C)(O)C1.O=C(O)c1cccnc1Cl | CN1CC(C)(CCCl)Oc2ncccc2C1=O.Cl | null | null | null | Acylation | OtherReaction | 438615aaa7c67c86d9535b47b3b7b90895cfd938eb5b9a43590840d2835a2eaa | 0eb6298bc44bc2b383aa42afc4dbdd5fb5155671f80555f7d307ebee31e1f5c0 | O=C1NCCOc2ncccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Cl;H0;D1;+0:6]):[#7;a:7]:[c:8].[C;D1;H3:9]-[N;H0;D3;+0:10]1-[C:11]-[C:12](-[C;D1;H3:13])(-[OH;D1;+0:14])-[C:15]-[CH2;D2;+0:16]-1>>[C;D1;H3:9]-[N;H0;D3;+0:10]1-[C:11]-[C:12](-[C;D1;H3:13])(-[C:15]-[CH2;D2;+0:16]-[Cl;H0;D1;+0:6])-[O;H0;D2;+0:14]-[c;H0;D3;+0:5]... | 10 | [{"value": 10.0, "product": "Cl.ClCCC1(OC2=C(C(N(C1)C)=O)C=CC=N2)C", "details": "PERCENTYIELD", "is_desired": false}] | 77 | CELSIUS | 8 | HOUR | To a suspension of 60 g (60% in oil, 1.5 mole) of sodium hydride in 400 ml of tetrahydrofuran heated to reflux was added a solution of 110 g (0.70 mole) of 2-chloronicotinic acid and 80 (0.70 mole) of 1,3-dimethyl-3-pyrrolidinol so as to maintain good reflux. Heating at reflux was continued overnight. The mass spectra ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Tertiary alcohol.Tertiary amine | Primary halide.Ether.Tertiary amide | C1CC[NH]C1.c1ccncc1 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | null | null | 77 | 8 | CN1CCC(C)(O)C1.O=C(O)c1cccnc1Cl>>CN1CC(C)(CCCl)Oc2ncccc2C1=O.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-969df2bb37174a8b86b8541a3ae806a4 | CN1CC(CCCl)Oc2cc3ccccc3nc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2cc3ccccc3nc2C1=S | ClCCC1OC=2C(=NC=3C=CC=CC3C2)C(N(C1)C)=O.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClCCC1OC=2C(=NC=3C=CC=CC3C2)C(N(C1)C)=S | O=[C:19]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17][c:18]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:20])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17][c:18]2[C:19]1=[S:20] | CN1CC(CCCl)Oc2cc3ccccc3nc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2cc3ccccc3nc2C1=S | null | null | C(C)#N.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | e784457bf758d431573169c722031f6d35830e2503345896e0e42caba7d885fd | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2cc3ccccc3nc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[#7;a:6]:[c:7]):[c:8]-[#8:9].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:10])(-S-2)-S-3>>[#8:9]-[c:8]:[c:5](:[#7;a:6]:[c:7])-[C;H0;D3;+0:1](=[S;H0;D1;+0:10])-[#7:2](-[C;D1;H3:3])-[C:4] | 86.9 | [{"value": 52.0, "product": "ClCCC1OC=2C(=NC=3C=CC=CC3C2)C(N(C1)C)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "ClCCC1OC=2C(=NC=3C=CC=CC3C2)C(N(C1)C)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 3.0 g (0.01 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-b]-quinolin-5(4H)-one in 30 ml of acetonitrile was added 1.3 g (0.006 mole) of phosphorus pentasulfide. The mixture was stirred vigorously at reflux for 2 hr. After cooling, the reaction mixture was diluted with 60 ml of toluene and filter... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2nc3c(cc2c1)OCC[NH]C3.S1P2SP3SP1SP(S2)S3 | c1ccc2nc3c(cc2c1)OCC[NH]C3 | c1ccc2nc3c(cc2c1)OCC[NH]C3 | Other | C(C)#N.C1(=CC=CC=C1)C | null | null | CN1CC(CCCl)Oc2cc3ccccc3nc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C(C)#N.C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2cc3ccccc3nc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-93749aa381254392b61d61749772cb78 | CN1CCC(O)C1.O=C(O)c1c(Cl)cncc1Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CN1Cc2c(Cl)cncc2OC(CCCl)C1.O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Cl)(Cl)(Cl)Cl.[H-].[Na+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Cl)(Cl)(Cl)Cl.CN1CC(CC1)O.ClC=1C=NC=C(C1C(=O)O)Cl>>ClC1=CN=CC2=C1CN(CC(O2)CCCl)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O | [CH3:1][N:2]1[CH2:3][CH2:13][CH:12]([OH:11])[CH2:16]1.O[C:14]([c:4]1[c:5]([Cl:6])[cH:7][n:8][cH:9][c:10]1[Cl:15])=[O:17].c1ccc(P(c2ccccc2)[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)cc1.c1ccc([P:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)cc1>>[CH3:1][N:2]1[CH2:3][c:4]2[c... | CN1CCC(O)C1.O=C(O)c1c(Cl)cncc1Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | CN1Cc2c(Cl)cncc2OC(CCCl)C1.O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | CN(C=O)C.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | aa75494d3c8cc5852672fc746a29df809e506396b90c8c63cd244985800cc08f | d89c6255ff7e0a1f92df0e88d8a75c65b37e0288b3d5758af16f3a275b2ebcab | O=P(c1ccccc1)(c1ccccc1)c1ccccc1.c1cc2c(cn1)OCCNC2 | O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c;H0;D3;+0:3]1:[c:4](-[Cl;D1;H0:5]):[c:6]:[#7;a:7]:[c:8]:[c;H0;D3;+0:9]:1-[Cl;H0;D1;+0:10].[C;D1;H3:11]-[#7:12]1-[C:13]-[C:14](-[OH;D1;+0:15])-[CH2;D2;+0:16]-[CH2;D2;+0:17]-1.[c:18]:[c:19](-[P;H0;D3;+0:20](-[c:21](:[c:22]):[c:23])-c1:c:c:c:c:c:1):[c:24].[c:25]:[c:26]:[c;H0;D3;+0:27](-... | null | [] | 60 | CELSIUS | 1 | HOUR | To a suspension of 2.1 g (60% in oil, 0.052 mole) of sodium hydride in 125 ml of dimethylformamide heated to 60° C. under a nitrogen gas blanket was added a solution of 2.65 g (0.026 mole) of N-methyl-3-pyrrolidinol and 5.0 g (0.026 mole) of 3,5-dichloropyridine-4-carboxylic acid in 40 ml of dimethylformamide dropwise ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Secondary alcohol | Primary halide.Ether | C1CC[NH]C1.c1ccncc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1cc2c(cn1)OCC[NH]C2.c1ccccc1 | c1cc2c(cn1)OCC[NH]C2.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C=O)C.C(C)N(CC)CC | 60 | 1 | CN1CCC(O)C1.O=C(O)c1c(Cl)cncc1Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>CN(C=O)C.C(C)N(CC)CC>CN1Cc2c(Cl)cncc2OC(CCCl)C1.O=P(c1ccccc1)(c1ccccc1)c1ccccc1 |
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