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-c34472859da14a81bfe0f74e60f15c43 | ord-61053f41062346ee89796604b2fcc8cc | COC(=O)c1ccccc1S(=O)(=O)NC(=O)NN1N=C(OC)C=C(C)N1.CS>>COC1=NN(NC(=O)NS(=O)(=O)c2ccccc2C(=O)SC)NC(C)=C1 | C[Al](C)C.COC1=NN(NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC.CS>>COC1=NN(NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)SC | CO[C:19]([c:18]1[c:13]([S:10]([NH:9][C:7]([NH:6][N:5]2[N:4]=[C:3]([O:2][CH3:1])[CH:26]=[C:24]([CH3:25])[NH:23]2)=[O:8])(=[O:11])=[O:12])[cH:14][cH:15][cH:16][cH:17]1)=[O:20].[SH:21][CH3:22]>>[CH3:1][O:2][C:3]1=[N:4][N:5]([NH:6][C:7](=[O:8])[NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19](=... | COC(=O)c1ccccc1S(=O)(=O)NC(=O)NN1N=C(OC)C=C(C)N1.CS | COC1=NN(NC(=O)NS(=O)(=O)c2ccccc2C(=O)SC)NC(C)=C1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | c823aed818d01e122d4213eef16971b16859047f24c9408150d480c9cbf7c870 | 46b20de9e98593a3c8a090991815ec74dc6f5a01657f01a6f6db1ed958280181 | O=C(NN1N=CC=CN1)NS(=O)(=O)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[SH;D1;+0:7]>>[C;D1;H3:6]-[S;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | Trimethylaluminum (6.0 m, 2M) was charged via syringe to 15 ml dry toluene under nitrogen atmosphere and 3.8 g N-[(4-methoxy-6-methyltriazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide was added portionwise. After stirring at room temperature for one hour, methyl mercaptan (gas) was passed through the react... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aliphatic thiol | Carbo-thioester | null | null | C1=CN[NH]N=C1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)NN1N=C(OC)C=C(C)N1.CS>C1(=CC=CC=C1)C>COC1=NN(NC(=O)NS(=O)(=O)c2ccccc2C(=O)SC)NC(C)=C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e9a338a0ae7346b69c18015f5e921efb | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1.[CH3][Al]([CH3])[CH3]>>CCCCSC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | C[Al](C)C.COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC>>COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)SCCCC | O([CH3:4])[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:5](=[O:15])(=[O:16])[NH:17][C:18](=[O:19])[NH:20][c:21]1[n:22][c:23]([CH3:24])[cH:25][c:26]([O:27][CH3:28])[n:29]1.[Al]([CH3:1])([CH3:2])[CH3:3]>>[CH3:1][CH2:2][CH2:3][CH2:4][S:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14](=[O:15])(=[O:16... | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1.[CH3][Al]([CH3])[CH3] | CCCCSC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 278ae0d28540c9554333d1751c4d8864b8f05ad2e43bfc48a420bf0664bdbb56 | f9b8b2b39f1824e0bcab4a130c63b5122605294cff8ca1aa0ec1553a229324e0 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [#7;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[S;H0;D4;+0:7](=[O;H0;D1;+0:8])(=[O;H0;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[C;H0;D3;+0:14](=[O;D1;H0:15])-O-[CH3;D1;+0:16]):[c:17]):[#7;a:18].[CH3;D1;+0:19]-[Al](-[CH3;D1;+0:20])-[CH3;D1;+0:21]>>[#7;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]... | 109.6 | [{"value": 109.6, "product": "COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)SCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Trimethylaluminum (1.5 ml) (2M) was charged via syringe to 5.0 ml dry toluene under nitrogen atmosphere and 0.54 g (0.006 mole) N-butanethiol in 2.0 ml toluene was added dropwise. N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide (0.95 g) was added portionwise and the mixture warme... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ester.Urea | Sulfonamide.Urea.Carbo-thioester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1 | HO- | C1(=CC=CC=C1)C | 80 | null | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1.[CH3][Al]([CH3])[CH3]>C1(=CC=CC=C1)C>CCCCSC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5bcbc2ae42f84511be9feb50b314ff77 | CC(C)S.COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=S)C(C)C)n1 | COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC.C[Al](C)C.CC(C)S.C1(=CC=CC=C1)C.C1(=CC=CC=C1)C.Cl.[Al]>>COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=S)C(C)C | [SH:23][CH:24]([CH3:25])[CH3:26].CO[C:22](=O)[c:21]1[c:16]([S:13]([NH:12][C:10]([NH:9][c:8]2[n:7][c:5]([CH3:6])[n:4][c:3]([O:2][CH3:1])[n:27]2)=[O:11])(=[O:14])=[O:15])[cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18]... | CC(C)S.COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 | COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=S)C(C)C)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 36827b64c13cf65c6e52cebaa9062cdf58fab985f2c9cdbf979bb47a3868d38c | f21a09760a88a80841695969620085328ea5d75a4ab5df4999a2de5bb620d932 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | C-O-[C;H0;D3;+0:1](=O)-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[CH;D3;+0:6](-[C;D1;H3:7])-[SH;D1;+0:8]>>[C;D1;H3:5]-[CH;D3;+0:6](-[C;D1;H3:7])-[C;H0;D3;+0:1](=[S;H0;D1;+0:8])-[c:2](:[c:3]):[c:4] | null | [] | 80 | CELSIUS | null | null | To 1.5 ml (2N) trimethylaluminum in 5 ml dry toluene under N2 was added dropwise 0.48 g (6.0 mmole) 2-propanethiol in 2 ml toluene. The resultant aluminum reagent was stirred at room temperature for 15 minutes, and 0.95 g (2.5 mmole) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aliphatic thiol | Thiocarbonyl | null | null | c1ncncn1.c1ccccc1 | HO- | null | 80 | null | CC(C)S.COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=S)C(C)C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-110a99ca22d24d1aaa8b04b13f3b40fe | C#CCCC(OC)OC>>COC(CCC#[C][Mg][Br])OC | C(C)[Mg]Br.COC(CCC#C)OC>>COC(CCC#C[Mg]Br)OC | [CH3:1][O:2][CH:3]([CH2:4][CH2:5][C:6]#[CH:7])[O:10][CH3:11]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][C:6]#[C:7][Mg:8][Br:9])[O:10][CH3:11] | C#CCCC(OC)OC | COC(CCC#[C][Mg][Br])OC | null | null | null | Functional Group Addition | OtherReaction | 9ee88fed8ce2e777f24e2977a558b191e713a084ba43290013a977f15ef34d66 | 953195a21f5b48bf1869677fd531d455a389a1b193f9dd48f73a8504fbfe487a | null | [C:1]-[C:2]#[CH;D1;+0:3]>>[Br;D1;H0:4]-[#12:5]-[C;H0;D2;+0:3]#[C:2]-[C:1] | null | [] | null | null | null | null | 1,1-dimethoxy-pent-4-yn-5-yl magnesium bromide was prepared in situ from ethyl magnesium bromide and 1,1-dimethoxy-4-pentyne. The latter was prepared as follows:
Conditions: See reaction.notes.procedure_details.
Workup: The latter was prepared | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Magnesium halide.Alkyne | null | null | null | null | null | null | null | C#CCCC(OC)OC>>COC(CCC#[C][Mg][Br])OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9aceded8345a480cbb20b84ecb25dc5a | COC(CCBr)OC.[C-]#[C-]>>C#CCCC(OC)OC | N.[C-]#[C-].[Li+].[Li+].N.BrCCC(OC)OC>>COC(CCC#C)OC | Br[CH2:3][CH2:4][CH:5]([O:6][CH3:7])[O:8][CH3:9].[C-:1]#[C-:2]>>[CH:1]#[C:2][CH2:3][CH2:4][CH:5]([O:6][CH3:7])[O:8][CH3:9] | COC(CCBr)OC.[C-]#[C-] | C#CCCC(OC)OC | null | null | null | C-C Coupling | OtherReaction | 66a66c6d9d223d8c996186abb1c3363aa1cdd7601651e1be69c579c9d82fc938 | 8b7158609d43c44b33cd29cbcb76286ab06895f1beb89c8feddf0097884caf0a | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C-;H0;D1:4]#[C-;H0;D1:5]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D2;+0:5]#[CH;D1;+0:4] | null | [] | null | null | 2 | HOUR | To an equivalent quantity of lithium acetylide in liquid NH3 55 g (0.3 mol) of 1-bromo-3,3-dimethoxypropane were added in 30 minutes. Subsequently, stirring was continued for a further 2 hours, after which the NH3 was allowed to evaporate and the residue was dissolved in a mixture of ice and water. The mixture was extr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Alkyne | null | null | null | Br- | null | null | 2 | COC(CCBr)OC.[C-]#[C-]>>C#CCCC(OC)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1ef2a53333f948fbaba0c8b3aaad3e06 | C=CCOC(=O)C(=C)C>>C=CCOC(=O)C(=C)C | C(C(=C)C)(=O)OCC=C.C(C(=C)C)(=O)O.N(=NC(C#N)(CC(C)C)C)C(C#N)(CC(C)C)C>>C(C(=C)C)(=O)OCC=C.C(C(=C)C)(=O)O | [CH2:7]=[CH:8][CH2:9][O:10][C:11](=[O:12])[C:13](=[CH2:14])[CH3:15]>>[CH2:7]=[CH:8][CH2:9][O:10][C:11](=[O:12])[C:13](=[CH2:14])[CH3:15] | C=CCOC(=O)C(=C)C | C=CCOC(=O)C(=C)C | null | null | ClCCCl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 70 | CELSIUS | 2 | HOUR | The poly(allyl methacrylate/methacrylic acid) was synthesized by the following process. In a 3 l four-necked flask equipped with a stirring bar and a stirring blade, a reflux condenser, a dropping funnel and a thermometer, 1.68 l of 1,2-dichloroethane was placed as a reaction solvent and heated to 70° C. in a nitrogen ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | ClCCCl | 70 | 2 | C=CCOC(=O)C(=C)C>ClCCCl>C=CCOC(=O)C(=C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cff468f4f07445f5a8898cf0f4e36580 | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>O=C(CO)[C@@H](O)[C@H](O)[C@H](O)CO | [O-]S(=O)(=O)[O-].[Mg+2].O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O)O.O.C(=O)(O)[O-].[Na+].C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O)O.O>>OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO | [OH:1][C@@H:2]([CH:3]=[O:4])[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@H:9]([OH:10])[CH2:11][OH:12]>>[O:1]=[C:2]([CH2:3][OH:4])[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@H:9]([OH:10])[CH2:11][OH:12] | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | O=C(CO)[C@@H](O)[C@H](O)[C@H](O)CO | null | null | O | Miscellaneous | OtherReaction | da1d84dbe1e04a618884415ce52b4d15782620dd1190cbd5660bd9f02aefd426 | b43f9cdbe1116b8813ece77fa48d784d24ee5e86989234069a29d070c300f6f8 | null | [C:1]-[C:2](-[O;D1;H1:3])-[C@@H;D3;+0:4](-[OH;D1;+0:5])-[CH;D2;+0:6]=[O;H0;D1;+0:7]>>[C:1]-[C:2](-[O;D1;H1:3])-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[CH2;D2;+0:6]-[OH;D1;+0:7] | null | [] | 60 | CELSIUS | null | null | This example describes the application of the immobilized glucose isomerase produced from DSM 3253. 11.7 g of the dried granulate produced in Example 6 was soaked in 200 ml 45% w/w glucose syrup, pH 7.5 for two hours. The enzyme particles were then transferred to a water jacketed column and a 45% w/w glucose syrup with... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary alcohol | Ketone.Primary alcohol | null | null | null | null | O | 60 | null | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>O>O=C(CO)[C@@H](O)[C@H](O)[C@H](O)CO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-991606544acc4eb9b91f50e9dac2e1ee | CN1C(C(=O)Nc2ccccn2)=C(O)c2ccccc2S1(=O)=O.Cc1cc(NC(=O)C2=C(O)c3ccccc3S(=O)(=O)N2C)no1>>CN1C(C(=O)Nc2nccs2)=C(O)c2ccccc2S1(=O)=O | CC1=CC(=NO1)NC(=O)C2=C(C=3C=CC=CC3S(=O)(=O)N2C)O.CN1C(=C(C=2C=CC=CC2S1(=O)=O)O)C(=O)NC=3C=CC=CN3>>OC1=C(N(S(C2=C1C=CC=C2)(=O)=O)C)C(=O)NC=2SC=CN2 | c1c[cH:10][cH:9][n:8][c:7]1[NH:6][C:4]([C:3]1=[C:12]([OH:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[S:20](=[O:21])(=[O:22])[N:2]1[CH3:1])=[O:5].Cc1cc(NC(=O)C2=C(O)c3ccccc3[S:11](=O)(=O)N2C)no1>>[CH3:1][N:2]1[C:3]([C:4](=[O:5])[NH:6][c:7]2[n:8][cH:9][cH:10][s:11]2)=[C:12]([OH:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][... | CN1C(C(=O)Nc2ccccn2)=C(O)c2ccccc2S1(=O)=O.Cc1cc(NC(=O)C2=C(O)c3ccccc3S(=O)(=O)N2C)no1 | CN1C(C(=O)Nc2nccs2)=C(O)c2ccccc2S1(=O)=O | null | null | null | Miscellaneous | OtherReaction | fb9e4592484c3201fc1921ce30330a465cfd73e4ae3f678f2ae5d0f95b0155c7 | f8a254218156fd20c1c93cd3db193e0f26a7a7b4497175012fb748f6223061a2 | O=C(Nc1nccs1)C1=Cc2ccccc2S(=O)(=O)N1 | C-N1-C(-C(=O)-N-c2:c:c(-C):o:n:2)=C(-O)-c2:c:c:c:c:c:2-[S;H0;D4;+0:1]-1(=O)=O.[#7:2]-[C:3](-[C:4](=[O;D1;H0:5])-[#7:6]-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[cH;D2;+0:10]:c:c:1)=[C:11]>>[#7:2]-[C:3](-[C:4](=[O;D1;H0:5])-[#7:6]-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[cH;D2;+0:10]:[s;H0;D2;+0:1]:1)=[C:11] | null | [] | null | null | null | null | The oxicams may be combined with the special 1,2-diacyl-glycero-3-phosphocholines in a molar ratio of 1:1 to 1:20, preferably in a molar ratio of 1:1 to 1:10. A unit dose for the therapeutic application to humans amounts to 5-300 mg oxicam combined with 10-500 mg 1,2-diacyl-glycerol-3-phosphocholine per day, preferably... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Secondary amide.Enol | null | c1ccncc1.c1cnoc1.C1=Cc2ccccc2SN1 | c1cscn1 | c1cscn1.C1=Cc2ccccc2S[NH]1 | HO- | null | null | null | CN1C(C(=O)Nc2ccccn2)=C(O)c2ccccc2S1(=O)=O.Cc1cc(NC(=O)C2=C(O)c3ccccc3S(=O)(=O)N2C)no1>>CN1C(C(=O)Nc2nccs2)=C(O)c2ccccc2S1(=O)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9e3f18cd9f6049a2b27c425d1d3375db | O=C(O)CCc1c[nH]cn1.OP(O)O>>O=P(O)(O)C(O)(CCc1c[nH]cn1)P(=O)(O)O | Cl.N1C=NC(=C1)CCC(=O)O.P(O)(O)O.P(Cl)(Cl)Cl>>OC(CCC=1N=CNC1)(P(O)(=O)O)P(O)(=O)O | [O:1]=[C:5]([OH:6])[CH2:7][CH2:8][c:9]1[cH:10][nH:11][cH:12][n:13]1.[P:14]([OH:15])([OH:16])[OH:17]>>[O:1]=[P:2]([OH:3])([OH:4])[C:5]([OH:6])([CH2:7][CH2:8][c:9]1[cH:10][nH:11][cH:12][n:13]1)[P:14](=[O:15])([OH:16])[OH:17] | O=C(O)CCc1c[nH]cn1.OP(O)O | O=P(O)(O)C(O)(CCc1c[nH]cn1)P(=O)(O)O | null | null | ClC1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | fbe672564179bd9e3cdb7674d18b78c96802803672548bbaf63d8ec4789a0133 | 2ce4f2eee8b5c87b9534d27756d55653dd16ea5ef20283a7ae054d7de47ecf10 | c1c[nH]cn1 | [C:1]-[C:2]-[C;H0;D3;+0:3](-[O;D1;H1:4])=[O;H0;D1;+0:5].[O;D1;H1:6]-[P;H0;D3;+0:7](-[O;D1;H1:8])-[OH;D1;+0:9]>>[C:1]-[C:2]-[C;H0;D4;+0:3](-[O;D1;H1:4])(-[#15:10](-[O;D1;H1:11])(-[O;D1;H1:12])=[O;H0;D1;+0:5])-[P;H0;D4;+0:7](-[O;D1;H1:6])(-[O;D1;H1:8])=[O;H0;D1;+0:9] | null | [] | null | null | 4 | HOUR | 3.53 g. (20 mMol) 3-(4-imidazolyl)-propionic acid hydrochloride are heated with 2.26 g. phosphorous acid in 10 ml. chlorobenzene to 110° C., while stirring. 4.12 g. (30 mMol) phosphorus trichloride are slowly added dropwise thereto and heating continued for 4 hours at 110° C. After cooling, the chlorobenzene is decante... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Tertiary alcohol | null | null | c1c[nH]cn1 | null | ClC1=CC=CC=C1 | null | 4 | O=C(O)CCc1c[nH]cn1.OP(O)O>ClC1=CC=CC=C1>O=P(O)(O)C(O)(CCc1c[nH]cn1)P(=O)(O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4819b5e5895e4960952ecc255abd55df | N#Cc1ccc(Cn2cc(C=CC(=O)O)nn2)cc1>>N#Cc1ccc(Cn2cc(C=CC=O)nn2)cc1 | NCC1=CC=C(CN2N=NC(=C2)CCC(=O)O)C=C1.C(#N)C1=CC=C(CN2N=NC(=C2)C=CC(=O)O)C=C1>>C(#N)C1=CC=C(CN2N=NC(=C2)C=CC=O)C=C1 | O=[C:13]([CH:12]=[CH:11][c:10]1[cH:9][n:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17]2)[n:16][n:15]1)[OH:14]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][c:10]([CH:11]=[CH:12][CH:13]=[O:14])[n:15][n:16]2)[cH:17][cH:18]1 | N#Cc1ccc(Cn2cc(C=CC(=O)O)nn2)cc1 | N#Cc1ccc(Cn2cc(C=CC=O)nn2)cc1 | null | null | null | Miscellaneous | OtherReaction | 148369763d5ac94fa638d0416b05b2817b88fbcf3e3881a34df5b1c1422931df | 8efb0e76025bf10ceb3c462bb2943eb84b6953d35e82203a100aa1bb9e5b03cd | c1ccc(Cn2ccnn2)cc1 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[C:3]=[C:4]-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[c:9]:1>>[O;H0;D1;+0:2]=[CH;D2;+0:1]-[C:3]=[C:4]-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[c:9]:1 | 41 | [{"value": 41.0, "product": "C(#N)C1=CC=C(CN2N=NC(=C2)C=CC=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-[1-(4-aminomethylbenzyl)-1,2,3-triazol-4-yl]-propionic acid (m.p. 207°-210° C.; prepared by catalytic hydrogenation of 3-[1-(4-cyanobenzyl)-1,2,3-triazol-4-yl]-acrylic acid (m.p. 168°-170° C.) which is obtained by oxidation of the corresponding 3-[1-(4-cyanobenzyl)-1,2,3-triazol-4-yl]-acrolein (m.p. 152°-155° C.)):
C... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aldehyde | null | null | c1ccccc1.c1c[nH]nn1 | Other | null | null | null | N#Cc1ccc(Cn2cc(C=CC(=O)O)nn2)cc1>>N#Cc1ccc(Cn2cc(C=CC=O)nn2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c38af45d8c8949a08506bae42aea1f0f | O=C(O)C=Cc1cn(Cc2cccc([N+](=O)[O-])c2)nn1>>O=CC=Cc1cn(Cc2cccc([N+](=O)[O-])c2)nn1 | [N+](=O)([O-])C=1C=C(CN2N=NC(=C2)CCC(=O)O)C=CC1.NOS(=O)(=O)O.[N+](=O)([O-])C=1C=C(CN2N=NC(=C2)C=CC(=O)O)C=CC1>>[N+](=O)([O-])C=1C=C(CN2N=NC(=C2)C=CC=O)C=CC1 | O[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][n:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]2)[n:18][n:19]1>>[O:1]=[CH:2][CH:3]=[CH:4][c:5]1[cH:6][n:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]2)[n:18][n:19]1 | O=C(O)C=Cc1cn(Cc2cccc([N+](=O)[O-])c2)nn1 | O=CC=Cc1cn(Cc2cccc([N+](=O)[O-])c2)nn1 | null | null | null | Reduction | OtherReaction | 78999da0d33b2c10ff8c3d41626c41ea14d2697ff6d1d7e5baf78453ec38592a | f41d7c101137b93550fdf296ceb4547d1ce640e4cbceb5b7b006723d153456c9 | c1ccc(Cn2ccnn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[c:9]:1>>[O;D1;H0:2]=[CH;D2;+0:1]-[C:3]=[C:4]-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[c:9]:1 | 22 | [{"value": 22.0, "product": "[N+](=O)([O-])C=1C=C(CN2N=NC(=C2)C=CC=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-[1-(3-nitrobenzyl)-1,2,3-triazol-4-yl]-propionic acid (m.p. 147°-150° C.; prepared by reduction by means of hydroxylamine-O-sulphonic acid of 3-[1-(3-nitrobenzyl)-1,2,3-triazol-4-yl]-acrylic acid (m.p. 155°-158° C.), which is obtained by oxidation of the corresponding 3-[1-(3-nitrobenzyl)-1,2,3-triazol-4-yl]-acrolein... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aldehyde | null | null | c1c[nH]nn1.c1ccccc1 | Other | null | null | null | O=C(O)C=Cc1cn(Cc2cccc([N+](=O)[O-])c2)nn1>>O=CC=Cc1cn(Cc2cccc([N+](=O)[O-])c2)nn1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-68f1d2b288a04771b06b3a0250f9d7d9 | CC(Br)CCBr.CC(C)C(C(C)C)(C(C)C)C(C)C.O=[PH](O)O[PH](=O)O>>CC1CCC1(P(=O)(O)O)P(=O)(O)O | P(=O)(O)OP(=O)O.C(C)(C)C(C(C)C)(C(C)C)C(C)C.BrCCC(C)Br>>CC1C(CC1)(P(O)(=O)O)P(O)(=O)O | Br[CH:2]([CH3:1])[CH2:3][CH2:4]Br.CC(C)[C:5](C(C)C)(C(C)C)C(C)C.[PH:6](=[O:7])([O:8][PH:10](=[O:11])[OH:13])[OH:9]>>[CH3:1][CH:2]1[CH2:3][CH2:4][C:5]1([P:6](=[O:7])([OH:8])[OH:9])[P:10](=[O:11])([OH:12])[OH:13] | CC(Br)CCBr.CC(C)C(C(C)C)(C(C)C)C(C)C.O=[PH](O)O[PH](=O)O | CC1CCC1(P(=O)(O)O)P(=O)(O)O | null | null | null | C-C Coupling | OtherReaction | 1258baffd45b2c5479a93fb378198c34aa13a76c5a5fea5261b40966616f18f6 | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | C1CCC1 | Br-[CH2;D2;+0:1]-[C:2]-[CH;D3;+0:3](-Br)-[C;D1;H3:4].C-C(-C)-[C;H0;D4;+0:5](-C(-C)-C)(-C(-C)-C)-C(-C)-C.[O;D1;H0:6]=[PH;D3;+0:7](-[O;D1;H1:8])-[O;H0;D2;+0:9]-[PH;D3;+0:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[C;D1;H3:4]-[CH;D3;+0:3]1-[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:5]-1(-[P;H0;D4;+0:7](=[O;D1;H0:6])(-[O;D1;H1:13])-[O;D1;H1:8]... | null | [] | null | null | null | null | Using the procedure of Example I, tetraisopropyl methane diphosphonate was converted to tetraisopropyl 2-methyl cyclobutane-1,1 diphosphonate by reaction with 1,3 dibromobutane at 80° C. for 4 hours. 31P NMR (CDCl3) chemical shift 24.1 ppm.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | null | C1CCC1 | C1CCC1 | HBr | null | null | null | CC(Br)CCBr.CC(C)C(C(C)C)(C(C)C)C(C)C.O=[PH](O)O[PH](=O)O>>CC1CCC1(P(=O)(O)O)P(=O)(O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a90e758761144eef9e5aad94c40127f7 | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)CCC(O)C1.ClC(Cl)(Cl)Cl>>O=P(O)(O)C1(P(=O)(O)O)CCC(Cl)C1 | OC1CC(CC1)(P(OC(C)C)(=O)OC(C)C)P(OC(C)C)(=O)OC(C)C.C(Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>ClC1CC(CC1)(P(O)(=O)O)P(O)(=O)O | CC(C)[O:3][P:2](=[O:1])([O:4]C(C)C)[C:5]1([P:6](=[O:7])([O:8]C(C)C)[O:9]C(C)C)[CH2:10][CH2:11][CH:12](O)[CH2:14]1.ClC(Cl)(Cl)[Cl:13]>>[O:1]=[P:2]([OH:3])([OH:4])[C:5]1([P:6](=[O:7])([OH:8])[OH:9])[CH2:10][CH2:11][CH:12]([Cl:13])[CH2:14]1 | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)CCC(O)C1.ClC(Cl)(Cl)Cl | O=P(O)(O)C1(P(=O)(O)O)CCC(Cl)C1 | null | null | null | Functional Group Interconversion | OtherReaction | ff9d76cf33655f7634de57c80188c20918d1cd463b570eb6b20cccb224566f96 | c5d1986c7739cb45a38ab13e0bb0baaa26f0b912c372cdfd930783053daebb51 | C1CCCC1 | C-C(-C)-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[O;H0;D2;+0:4]-C(-C)-C)-[C:5]1(-[#15:6](=[O;D1;H0:7])(-[O;H0;D2;+0:8]-C(-C)-C)-[O;H0;D2;+0:9]-C(-C)-C)-[C:10]-[C:11]-[CH;D3;+0:12](-O)-[C:13]-1.Cl-C(-Cl)(-Cl)-[Cl;H0;D1;+0:14]>>[Cl;H0;D1;+0:14]-[CH;D3;+0:12]1-[C:11]-[C:10]-[C:5](-[#15:2](=[O;D1;H0:3])(-[OH;D1;+0:1])-[OH;D1;... | 69 | [{"value": 69.0, "product": "ClC1CC(CC1)(P(O)(=O)O)P(O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Tetraisopropyl 3-hydroxycyclopentane-1,1-diphosphonate (3.00 g, 7.24 mmol) was dissolved in 50 mL dry CCl4. Triphenylphosphine (3.80 g, 14.5 mmol) was added and the mixture was refluxed for 72 h. The mixture was filtered, concentrated, and the residue chromatographed (3:2 hexane:THF) on silica gel to afford 2.15 g (69%... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Secondary alcohol | Secondary halide | C1CCCC1 | C1CCCC1 | C1CCCC1 | HCl | null | null | null | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)CCC(O)C1.ClC(Cl)(Cl)Cl>>O=P(O)(O)C1(P(=O)(O)O)CCC(Cl)C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4846f36cfef547aa941828cad3472d14 | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)CCCCCC1>>O=P(O)(O)C1(P(=O)(O)O)CCCCCC1 | C(C)(C)OP(=O)(OC(C)C)CP(OC(C)C)(=O)OC(C)C.C1(CCCCCC1)(P(OC(C)C)(=O)OC(C)C)P(OC(C)C)(=O)OC(C)C.BrCCCCCCBr.C1(CCCCCC1)(P(OC(C)C)(=O)OC(C)C)P(OC(C)C)(=O)OC(C)C.C(CCCCCCC(P(OC(C)C)(=O)OC(C)C)P(OC(C)C)(=O)OC(C)C)(P(OC(C)C)(=O)OC(C)C)P(OC(C)C)(=O)OC(C)C>>C1(CCCCCC1)(P(O)(=O)O)P(O)(=O)O | CC(C)[O:3][P:2](=[O:1])([O:4]C(C)C)[C:5]1([P:6](=[O:7])([O:8]C(C)C)[O:9]C(C)C)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1>>[O:1]=[P:2]([OH:3])([OH:4])[C:5]1([P:6](=[O:7])([OH:8])[OH:9])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)CCCCCC1 | O=P(O)(O)C1(P(=O)(O)O)CCCCCC1 | null | null | C1(=CC=CC=C1)C | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | C1CCCCCC1 | C-C(-C)-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[C:4]-[#15:5](=[O;D1;H0:6])(-[O;H0;D2;+0:7]-C(-C)-C)-[O;H0;D2;+0:8]-C(-C)-C)-[O;H0;D2;+0:9]-C(-C)-C>>[O;D1;H0:3]=[#15:2](-[OH;D1;+0:1])(-[OH;D1;+0:9])-[C:4]-[#15:5](=[O;D1;H0:6])(-[OH;D1;+0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | Using the same procedure as in Example I, tetraisopropyl methane diphosphonic acid was converted to tetraisopropyl cycloheptane-1,1-diphosphonate by reaction with 1,6-dibromohexane at 80° C. for 18 h. 31P NMR (toluene) indicated that the reaction solution contained a mixture of the desired tetraisopropyl cycloheptane-1... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCCCCC1 | Other | C1(=CC=CC=C1)C | null | null | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)CCCCCC1>C1(=CC=CC=C1)C>O=P(O)(O)C1(P(=O)(O)O)CCCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ed3aedf500114ff0af396ab94058498c | CC(C)OP(=O)(CP(=O)(OC(C)C)OC(C)C)OC(C)C.Cc1ccc(Br)c(Br)c1C>>O=P(O)(O)C1(P(=O)(O)O)Cc2ccccc2C1 | C(C)(C)OP(OC(C)C)(=O)CP(OC(C)C)(=O)OC(C)C.BrC=1C(=C(C(=CC1)C)C)Br>>C1C(CC2=CC=CC=C12)(P(O)(=O)O)P(O)(=O)O | CC(C)[O:3][P:2](=[O:1])([O:4]C(C)C)[CH2:5][P:6](=[O:7])([O:8]C(C)C)[O:9]C(C)C.Br[c:14]1[cH:13][cH:12][c:11]([CH3:10])[c:16]([CH3:17])[c:15]1Br>>[O:1]=[P:2]([OH:3])([OH:4])[C:5]1([P:6](=[O:7])([OH:8])[OH:9])[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17]1 | CC(C)OP(=O)(CP(=O)(OC(C)C)OC(C)C)OC(C)C.Cc1ccc(Br)c(Br)c1C | O=P(O)(O)C1(P(=O)(O)O)Cc2ccccc2C1 | null | null | null | C-C Coupling | OtherReaction | b80b0e94a8bfa3c4216641f8d9b7c5d3a2669301c430d4e8db692126d5694ccc | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc2c(c1)CCC2 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[CH3;D1;+0:5]):[c:6](-[CH3;D1;+0:7]):[c;H0;D3;+0:8]:1-Br.C-C(-C)-[O;H0;D2;+0:9]-[#15:10](=[O;D1;H0:11])(-[CH2;D2;+0:12]-[#15:13](=[O;D1;H0:14])(-[O;H0;D2;+0:15]-C(-C)-C)-[O;H0;D2;+0:16]-C(-C)-C)-[O;H0;D2;+0:17]-C(-C)-C>>[O;D1;H0:11]=[#15:10](-[OH;D1;+0:9])(-[OH;D1;+0:17])-[C;H0;D4;... | 70 | [{"value": 70.0, "product": "C1C(CC2=CC=CC=C12)(P(O)(=O)O)P(O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example I, tetraisopropylmethanediphosphonate MDP was converted to the desired ester in 70% yield by reaction with dibromo-o-xylene at 80° C. for 3 h: mp 55°-57° C.; 1H NMR (CDCl3) 7.15 (s, 4H, aromatic), 5.00-4.55 (m, 4H, CH), 3.60 (t, 4H, J=17.6 Hz, CH2), 1.26 (t, 24H, J=6 Hz, CH3); 3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccccc1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HBr | null | null | null | CC(C)OP(=O)(CP(=O)(OC(C)C)OC(C)C)OC(C)C.Cc1ccc(Br)c(Br)c1C>>O=P(O)(O)C1(P(=O)(O)O)Cc2ccccc2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d6ed2499815e4aea88f85497cd53146d | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)C=C2C=CNCC2=C1>>O=P(O)(O)C1(P(=O)(O)O)C=C2C=CNCC2=C1 | P(=O)(O)OP(=O)O.C(C)(C)C(C(C)C)(C(C)C)C(C)C.C1NC=CC2=CC(C=C12)(P(OC(C)C)(=O)OC(C)C)P(OC(C)C)(=O)OC(C)C.ClCC=1C=NC=CC1CCl>>C1NC=CC2=CC(C=C12)(P(O)(=O)O)P(O)(=O)O | CC(C)[O:3][P:2](=[O:1])([O:4]C(C)C)[C:5]1([P:6](=[O:7])([O:8]C(C)C)[O:9]C(C)C)[CH:10]=[C:11]2[CH:12]=[CH:13][NH:14][CH2:15][C:16]2=[CH:17]1>>[O:1]=[P:2]([OH:3])([OH:4])[C:5]1([P:6](=[O:7])([OH:8])[OH:9])[CH:10]=[C:11]2[CH:12]=[CH:13][NH:14][CH2:15][C:16]2=[CH:17]1 | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)C=C2C=CNCC2=C1 | O=P(O)(O)C1(P(=O)(O)O)C=C2C=CNCC2=C1 | null | null | null | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | C1=CC2=CCC=C2CN1 | C-C(-C)-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[O;H0;D2;+0:4]-C(-C)-C)-[C:5]1(-[#15:6](=[O;D1;H0:7])(-[O;H0;D2;+0:8]-C(-C)-C)-[O;H0;D2;+0:9]-C(-C)-C)-[C:10]=[C:11]-[C:12]=[C:13]-1>>[O;D1;H0:3]=[#15:2](-[OH;D1;+0:1])(-[OH;D1;+0:4])-[C:5]1(-[#15:6](=[O;D1;H0:7])(-[OH;D1;+0:8])-[OH;D1;+0:9])-[C:10]=[C:11]-[C:12]=[C:13]-1 | null | [] | null | null | null | null | Using the same procedure as in Example VII, tetraisopropyl methane diphosphonate is converted to tetraisopropyl dihydro-2-pyrindine-6,6-diphosphonate by reaction with 3,4-bis(chloromethyl)pyridine. The resulting ester is hydrolyzed as in Example VII to yield the dihydro-2-pyrindine-6,6-diphosphonic acid.
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1=CC2=CCC=C2CN1 | Other | null | null | null | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)C=C2C=CNCC2=C1>>O=P(O)(O)C1(P(=O)(O)O)C=C2C=CNCC2=C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0fdcf16ab5d14f69aa0f35ed9de5bfd6 | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)CC=CCC1>>O=P(O)(O)C1(P(=O)(O)O)CC=CCC1 | P(=O)(O)OP(=O)O.C(C)(C)C(C(C)C)(C(C)C)C(C)C.C1(CC=CCC1)(P(OC(C)C)(=O)OC(C)C)P(OC(C)C)(=O)OC(C)C.ClC\C=C/CCCl>>C1(CC=CCC1)(P(O)(=O)O)P(O)(=O)O | CC(C)[O:3][P:2](=[O:1])([O:4]C(C)C)[C:5]1([P:6](=[O:7])([O:8]C(C)C)[O:9]C(C)C)[CH2:10][CH:11]=[CH:12][CH2:13][CH2:14]1>>[O:1]=[P:2]([OH:3])([OH:4])[C:5]1([P:6](=[O:7])([OH:8])[OH:9])[CH2:10][CH:11]=[CH:12][CH2:13][CH2:14]1 | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)CC=CCC1 | O=P(O)(O)C1(P(=O)(O)O)CC=CCC1 | null | null | null | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | C1=CCCCC1 | C-C(-C)-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[C:4]-[#15:5](=[O;D1;H0:6])(-[O;H0;D2;+0:7]-C(-C)-C)-[O;H0;D2;+0:8]-C(-C)-C)-[O;H0;D2;+0:9]-C(-C)-C>>[O;D1;H0:3]=[#15:2](-[OH;D1;+0:1])(-[OH;D1;+0:9])-[C:4]-[#15:5](=[O;D1;H0:6])(-[OH;D1;+0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | Using the same procedure as in Example I, tetraisopropyl methane diphosphonate is converted to tetraisopropyl 3-cyclohexene-1,1-diphosphonate by reaction with 1,5-dichloro-cis-2-pentene. The resulting ester is hydrolyzed as in Example I to yield the 3-cyclohexene-1,1-diphosphonic acid.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1=CCCCC1 | Other | null | null | null | CC(C)OP(=O)(OC(C)C)C1(P(=O)(OC(C)C)OC(C)C)CC=CCC1>>O=P(O)(O)C1(P(=O)(O)O)CC=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0ed7cb4f3509415b89681d4cddec3600 | CCc1ccc(CCO)nc1.O=[N+]([O-])c1ccc(F)cc1>>CCc1ccc(CCOc2ccc([N+](=O)[O-])cc2)nc1 | O.C(C)C=1C=CC(=NC1)CCO.FC1=CC=C(C=C1)[N+](=O)[O-].[H-].[Na+]>>C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][OH:9])[n:19][cH:20]1.F[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[n:19][cH:20]1 | CCc1ccc(CCO)nc1.O=[N+]([O-])c1ccc(F)cc1 | CCc1ccc(CCOc2ccc([N+](=O)[O-])cc2)nc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCCc2ccccn2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 68.4 | [{"value": 62.9, "product": "C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2-(5-ethyl-2-pyridyl)ethanol (53.0 g) and 4-fluoronitrobenzene (47.0 g) in DMF (500 ml) was added portionwise under ice-cooling 60% sodium hydride in oil (16.0 g). The mixture was stirred under ice-cooling for one hour, then at room temperature for 30 minutes, poured into water and extracted with ether... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | HF | CN(C)C=O | null | 0.5 | CCc1ccc(CCO)nc1.O=[N+]([O-])c1ccc(F)cc1>CN(C)C=O>CCc1ccc(CCOc2ccc([N+](=O)[O-])cc2)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c3fa941edf5d4f6885bf7cdb75cdc2c3 | CCc1ccc(CCOc2ccc(CC(Br)C(=O)OC)cc2)nc1.NC(N)=S>>CCc1ccc(CCOc2ccc(CC3SC(=N)NC3=O)cc2)nc1 | NC(=S)N.BrC(C(=O)OC)CC1=CC=C(C=C1)OCCC1=NC=C(C=C1)CC.C(C)(=O)[O-].[Na+].C(C)O>>C(C)C=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=N)=O)C=C1 | CO[C:20]([CH:15](Br)[CH2:14][c:13]1[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:25][n:24]2)[cH:23][cH:22]1)=[O:21].[S:16]=[C:17]([NH2:18])[NH2:19]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH:15]3[S:16][C:17](=[NH:18])[NH:19][C:2... | CCc1ccc(CCOc2ccc(CC(Br)C(=O)OC)cc2)nc1.NC(N)=S | CCc1ccc(CCOc2ccc(CC3SC(=N)NC3=O)cc2)nc1 | null | null | null | Acylation | OtherReaction | 1fd135be618a0492e2f511f67a39d894f2f9fa2ef22e22f74f2aed74e1448a0b | 3a3941f49c1dd99ca645a85d83ee536a22d539c1489486c8005ac11062857c36 | N=C1NC(=O)C(Cc2ccc(OCCc3ccccn3)cc2)S1 | Br-[CH;D3;+0:1](-[C:2]-[c:3])-[C;H0;D3;+0:4](=[O;D1;H0:5])-O-C.[NH2;D1;+0:6]-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[S;H0;D1;+0:9]>>[NH;D1;+0:6]=[C;H0;D3;+0:7]1-[NH;D2;+0:8]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[CH;D3;+0:1](-[C:2]-[c:3])-[S;H0;D2;+0:9]-1 | 523 | [{"value": 523.0, "product": "C(C)C=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=N)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.5, "product": "C(C)C=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=N)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A mixture of the crude oil of methyl 2-bromo-3-{4-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}propionate (73.0 g) obtained in (b) thiourea (14.2 g), sodium acetate (15.3 g) and ethanol (500 ml) was stirred for 3 hours under reflux. The reaction mixture was concentrated under reduced pressure, and the concentrate wasneutralized... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Thiourea | Secondary amide.Monosulfide | null | C1CSCN1 | c1ccncc1.c1ccccc1.C1CSCN1 | HBr | null | null | 0.166667 | CCc1ccc(CCOc2ccc(CC(Br)C(=O)OC)cc2)nc1.NC(N)=S>>CCc1ccc(CCOc2ccc(CC3SC(=N)NC3=O)cc2)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0a9916073337443eb82f4d3e5056bb19 | Cc1ccc(CCOc2ccc([N+](=O)[O-])cc2)nc1>>Cc1ccc(CCOc2ccc(N)cc2)nc1 | CC=1C=CC(=NC1)CCOC1=CC=C(C=C1)[N+](=O)[O-]>>CC=1C=CC(=NC1)CCOC1=CC=C(N)C=C1 | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:17][n:16]2)[cH:15][cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]2)[n:16][cH:17]1 | Cc1ccc(CCOc2ccc([N+](=O)[O-])cc2)nc1 | Cc1ccc(CCOc2ccc(N)cc2)nc1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCCc2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 92.8 | [{"value": 92.5, "product": "CC=1C=CC(=NC1)CCOC1=CC=C(N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "CC=1C=CC(=NC1)CCOC1=CC=C(N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[2-(5-methyl-2-pyridyl)ethoxy]nitrobenzene (15.0 g) in methanol (150 ml) was subjected to catalytic reduction under 1 atmospheric pressure in the presence of 10% Pd-C (50% wet, 2.0 g). The catalyst was filtered off, and the filtrate was concentrated to give 4-[2-(5-methyl-2-pyridyl)ethoxy]aniline as cry... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | [Pd].CO | null | null | Cc1ccc(CCOc2ccc([N+](=O)[O-])cc2)nc1>[Pd].CO>Cc1ccc(CCOc2ccc(N)cc2)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-429220597d424f6884f08146deceabba | Br.C=CC(=O)OC.Cc1ccc(CCOc2ccc(N)cc2)nc1>>COC(=O)C(Br)Cc1ccc(OCCc2ccc(C)cn2)cc1 | N(=O)[O-].[Na+].CC=1C=CC(=NC1)CCOC1=CC=C(N)C=C1.Br.C(C=C)(=O)OC>>BrC(C(=O)OC)CC1=CC=C(C=C1)OCCC1=NC=C(C=C1)C | [BrH:6].[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:7].N[c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([CH3:19])[cH:20][n:21]2)[cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([Br:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([CH3:19])[cH:20][n:21]2)[cH:22][... | Br.C=CC(=O)OC.Cc1ccc(CCOc2ccc(N)cc2)nc1 | COC(=O)C(Br)Cc1ccc(OCCc2ccc(C)cn2)cc1 | null | null | O.CC(=O)C.CO | C-C Coupling | OtherReaction | fa6d89a11df1d51d550d71070755be72f9bdb83552839bba404de654836fff02 | 50a9d170f44f15d35e3a7d8ced3592a8de4e6e68b8b82ffc0f15a38f0aee2772 | c1ccc(OCCc2ccccn2)cc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[BrH;D0;+0:6].[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[CH2;D1;+0:12]>>[Br;H0;D1;+0:6]-[CH;D3;+0:11](-[CH2;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9](=[O;D1;H0:10])-[#8:8]-[C;D1;H3:7] | 87.5 | [{"value": 87.5, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 20 | MINUTE | To a mixture of 4-[2-(5-methyl-2-pyridyl)ethoxy]aniline (12.0 g), 47% aqueous HBr solution (36.5 g) and methanol (40 ml)-acetone (80 ml) was added dropwise a solution of NaNO2 (4.0 g) in water (10 ml) at 5° C. or below. The whole mixture was stirred at 5° C. for 20 minutes, then methyl acrylate (27.0 g) was added there... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Vinyl | Secondary halide.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | Other | O.CC(=O)C.CO | 5 | 0.333333 | Br.C=CC(=O)OC.Cc1ccc(CCOc2ccc(N)cc2)nc1>O.CC(=O)C.CO>COC(=O)C(Br)Cc1ccc(OCCc2ccc(C)cn2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-88bef02453eb4624af3bc3568e27ac9f | Cc1ccc(CCOc2ccc(CC3SC(=N)NC3=O)cc2)nc1>>Cc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1 | N=C1SC(C(N1)=O)CC1=CC=C(C=C1)OCCC1=NC=C(C=C1)C.Cl.C(O)([O-])=O.[Na+]>>CC=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1 | N=[C:16]1[S:15][CH:14]([CH2:13][c:12]2[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:24][n:23]3)[cH:22][cH:21]2)[C:19](=[O:20])[NH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][CH:14]3[S:15][C:16](=[O:17])[NH:18][C:19]3=[O:20])[cH:21][cH:22]2)[n:... | Cc1ccc(CCOc2ccc(CC3SC(=N)NC3=O)cc2)nc1 | Cc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | f046889ce8daaa16d703a486d3d37eebdf9db15bb1e3dd38420792f8223379ea | 7c5edfdc08a50b13c55b36efa2d88805a54ee805dca02159dcfea130e57cb3a6 | O=C1NC(=O)C(Cc2ccc(OCCc3ccccn3)cc2)S1 | N=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-1>>[O;D1;H0:7]=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-1 | 87.5 | [{"value": 87.5, "product": "CC=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-imino-5-{4-[2-(5-methyl-2-pyridyl)ethoxy]benzyl}-4-thiazolidinone (8.0 g), 2N HCl (80 ml) and ethanol (80 ml) was refluxed for 16 hours. The reaction solution was neutralized with a saturated aqueous solution of sodium hydrogencarbonate to yield crystals. The crystals were collected by filtration and rec... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Unsubstituted dicarboximide | C1CSCN1 | C1CSCN1 | c1ccncc1.c1ccccc1.C1CSCN1 | null | C(C)O | null | null | Cc1ccc(CCOc2ccc(CC3SC(=N)NC3=O)cc2)nc1>C(C)O>Cc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e3e9c4bec33d4446bc86662ed3a3f024 | C[C@H](NC(=O)OCc1ccccc1)C(=O)O.OC[C@@H]1CCCN1>>C[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C=O | C(C1=CC=CC=C1)OC(=O)N[C@@H](C)C(=O)O.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C)C(=O)N1[C@H](C=O)CCC1 | O[C:14]([C@H:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:15].[NH:16]1[CH2:17][CH2:18][CH2:19][C@H:20]1[CH2:21][OH:22]>>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14](=[O:15])[N:16]1[CH2:17][CH2:18][CH2:19][C@H:20]1[CH:21]=[O:22] | C[C@H](NC(=O)OCc1ccccc1)C(=O)O.OC[C@@H]1CCCN1 | C[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C=O | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | O=C(NCC(=O)N1CCCC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[OH;D1;+0:8]-[CH2;D2;+0:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[C;D1;H3:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[C:11]-[C:10]-1-[CH;D2;+0:9]=[O;H0;D1;+0:8] | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 22.3 g of N-benzyloxycarbonylalanine. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated until dryness whereby a semi-solid ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | C1CCOC1 | 4 | 21 | C[C@H](NC(=O)OCc1ccccc1)C(=O)O.OC[C@@H]1CCCN1>C1CCOC1>C[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1a1ecef91c5c4ef38f90f2b3fd8ee0d5 | O=C(O)CNC(=O)OCc1ccccc1.OC[C@@H]1CCCN1>>O=C[C@@H]1CCCN1C(=O)CNC(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)NCC(=O)O.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)OC(=O)NCC(=O)N1[C@H](C=O)CCC1 | O[C:8](=[O:9])[CH2:10][NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[OH:1][CH2:2][C@@H:3]1[CH2:4][CH2:5][CH2:6][NH:7]1>>[O:1]=[CH:2][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]1[C:8](=[O:9])[CH2:10][NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | O=C(O)CNC(=O)OCc1ccccc1.OC[C@@H]1CCCN1 | O=C[C@@H]1CCCN1C(=O)CNC(=O)OCc1ccccc1 | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | O=C(NCC(=O)N1CCCC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[OH;D1;+0:7]-[CH2;D2;+0:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[O;D1;H0:6]=[C:5]-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[C:10]-[C:9]-1-[CH;D2;+0:8]=[O;H0;D1;+0:7] | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 17.7 g of N-benzyloxycarbonyl-glycin. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated whereby a semi-solid substance was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HO- | C1CCOC1 | 4 | 21 | O=C(O)CNC(=O)OCc1ccccc1.OC[C@@H]1CCCN1>C1CCOC1>O=C[C@@H]1CCCN1C(=O)CNC(=O)OCc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e9313fdb88e642c69e0966f055622c1c | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OC[C@@H]1CCCN1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C=O | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)N1[C@H](C=O)CCC1 | O[C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17].[NH:18]1[CH2:19][CH2:20][CH2:21][C@H:22]1[CH2:23][OH:24]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[N:18]1[CH2:19][CH2:... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OC[C@@H]1CCCN1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C=O | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | O=C(NCC(=O)N1CCCC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[OH;D1;+0:8]-[CH2;D2;+0:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[C:11]-[C:10]-1-[CH;D2;+0:9]=[O;H0;D1;+0:8] | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 22.1 g of N-benzyloxycarbonylvaline. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated whereby a semi-solid substance was o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | C1CCOC1 | 4 | 21 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OC[C@@H]1CCCN1>C1CCOC1>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5fceb538396d473db07422c06f10d8a9 | O=C(O)[C@@H]1CCCN1C(=O)OCc1ccccc1.OC[C@@H]1CCCN1>>O=C[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)N1[C@H](C(=O)O)CCC1.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)OC(=O)N1[C@H](C(=O)N2[C@H](C=O)CCC2)CCC1 | O[C:8](=[O:9])[C@@H:10]1[CH2:11][CH2:12][CH2:13][N:14]1[C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[OH:1][CH2:2][C@@H:3]1[CH2:4][CH2:5][CH2:6][NH:7]1>>[O:1]=[CH:2][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]1[C:8](=[O:9])[C@@H:10]1[CH2:11][CH2:12][CH2:13][N:14]1[C:15](=[O:16])[O:17][CH2:18][c:19]1[c... | O=C(O)[C@@H]1CCCN1C(=O)OCc1ccccc1.OC[C@@H]1CCCN1 | O=C[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1 | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | O=C([C@@H]1CCCN1C(=O)OCc1ccccc1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9].[OH;D1;+0:10]-[CH2;D2;+0:11]-[C:12]1-[C:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[#8:7]-[C:6](=[O;D1;H0:8])-[#7:5](-[C:9])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[C:13]-[C:12]-1-[CH;D2;+0:11]=[O;H0;D1;+0:10])-[C... | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 22.1 g of N-benzyloxycarbonyl-proline. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated whereby a semi-solid substance was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.C1CC[NH]C1.c1ccccc1 | HO- | C1CCOC1 | 4 | 21 | O=C(O)[C@@H]1CCCN1C(=O)OCc1ccccc1.OC[C@@H]1CCCN1>C1CCOC1>O=C[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8752b99810224a1a914c377b38936662 | CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)O.OC[C@@H]1CCCN1>>CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C=O | C(C1=CC=CC=C1)OC(=O)N[C@@H](CC(C)C)C(=O)O.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)OC(=O)N[C@@H](CC(C)C)C(=O)N1[C@H](C=O)CCC1 | O[C:17]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[O:18].[NH:19]1[CH2:20][CH2:21][CH2:22][C@H:23]1[CH2:24][OH:25]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[N:1... | CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)O.OC[C@@H]1CCCN1 | CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C=O | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | O=C(NCC(=O)N1CCCC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[OH;D1;+0:8]-[CH2;D2;+0:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[C:11]-[C:10]-1-[CH;D2;+0:9]=[O;H0;D1;+0:8] | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 26.5 g of N-benzyloxycarbonyl-leucin. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated whereby a semi-solid substance was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | C1CCOC1 | 4 | 21 | CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)O.OC[C@@H]1CCCN1>C1CCOC1>CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3ef9bc1218394e92b48c4045c58b1eba | C[C@H](NC(=O)OC(C)(C)C)C(=O)O.OC[C@@H]1CCCN1>>C[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C=O | C(C)(C)(C)OC(=O)N[C@@H](C)C(=O)O.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C)(C)(C)OC(=O)N[C@@H](C)C(=O)N1[C@H](C=O)CCC1 | O[C:11]([C@H:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:12].[NH:13]1[CH2:14][CH2:15][CH2:16][C@H:17]1[CH2:18][OH:19]>>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[C:11](=[O:12])[N:13]1[CH2:14][CH2:15][CH2:16][C@H:17]1[CH:18]=[O:19] | C[C@H](NC(=O)OC(C)(C)C)C(=O)O.OC[C@@H]1CCCN1 | C[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C=O | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[OH;D1;+0:13]-[CH2;D2;+0:14]-[C:15]1-[C:16]-[C:17]-[C:18]-[NH;D2;+0:19]-1>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:8]-[C:6](=[O;D1;H0:7])-[#7:5]-[C:3](-[C;D1;H3:4])-[C;H0;D3... | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 22.1 g of t-butyloxycarbonylalanine. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated whereby a semi-solid substance was o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | HO- | C1CCOC1 | 4 | 21 | C[C@H](NC(=O)OC(C)(C)C)C(=O)O.OC[C@@H]1CCCN1>C1CCOC1>C[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2ac0089866874d7e86e062b7f0f4369a | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O.OC[C@@H]1CCCN1>>CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C=O | C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N1[C@H](C=O)CCC1 | O[C:17]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[O:18].[NH:19]1[CH2:20][CH2:21][CH2:22][C@H:23]1[CH2:24][OH:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])... | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O.OC[C@@H]1CCCN1 | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C=O | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | O=C(CCc1ccccc1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[OH;D1;+0:13]-[CH2;D2;+0:14]-[C:15]1-[C:16]-[C:17]-[C:18]-[NH;D2;+0:19]-1>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D... | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 29.9 g of t-butyloxycarbonyl-phenylalanine. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated whereby a semi-solid substanc... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | C1CCOC1 | 4 | 21 | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O.OC[C@@H]1CCCN1>C1CCOC1>CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7405071ee847413aa73f043850a28c73 | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.OC[C@@H]1CCCN1>>CC(C)(C)OC(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C=O | C(C)(C)(C)OC(=O)N[C@@H](CO)C(=O)O.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C)(C)(C)OC(=O)N[C@@H](CO)C(=O)N1[C@H](C=O)CCC1 | O[C:12]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][OH:11])=[O:13].[NH:14]1[CH2:15][CH2:16][CH2:17][C@H:18]1[CH2:19][OH:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][OH:11])[C:12](=[O:13])[N:14]1[CH2:15][CH2:16][CH2:17][C@H:18]1[CH:19]=[O:20] | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.OC[C@@H]1CCCN1 | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C=O | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[OH;D1;+0:13]-[CH2;D2;+0:14]-[C:15]1-[C:16]-[C:17]-[C:18]-[NH;D2;+0:19]-1>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D... | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 20.5 g of t-butyloxycarbonylserine. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated whereby a semi-solid substance was ob... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | HO- | C1CCOC1 | 4 | 21 | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.OC[C@@H]1CCCN1>C1CCOC1>CC(C)(C)OC(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9496fbff4a6b482bac2e32cc8686d91d | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.OC[C@@H]1CCCN1>>CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCC[C@H]1C=O | C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)O.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N1[C@H](C=O)CCC1 | O[C:18]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1)=[O:19].[NH:20]1[CH2:21][CH2:22][CH2:23][C@H:24]1[CH2:25][OH:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1... | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.OC[C@@H]1CCCN1 | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCC[C@H]1C=O | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | O=C(CCc1ccccc1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[OH;D1;+0:13]-[CH2;D2;+0:14]-[C:15]1-[C:16]-[C:17]-[C:18]-[NH;D2;+0:19]-1>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D... | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 28.1 g of t-butyloxycarbonyltyrosine. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated whereby a semi-solid substance was ob... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | C1CCOC1 | 4 | 21 | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.OC[C@@H]1CCCN1>C1CCOC1>CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCC[C@H]1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d17c399d4d624da88d4df701a69906bc | CC(=O)NCC(=O)O.OC[C@@H]1CCCN1>>CC(=O)NCC(=O)N1CCC[C@H]1C=O | N1[C@H](CO)CCC1.C(C)(=O)NCC(=O)O.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C)(=O)NCC(=O)N1[C@H](C=O)CCC1 | O[C:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])=[O:7].[NH:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[CH2:13][OH:14]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[CH:13]=[O:14] | CC(=O)NCC(=O)O.OC[C@@H]1CCCN1 | CC(=O)NCC(=O)N1CCC[C@H]1C=O | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].[OH;D1;+0:8]-[CH2;D2;+0:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[C;D1;H3:6]-[C:5](=[O;D1;H0:7])-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[C:11]-[C:10]-1-[CH;D2;+0:9]=[O;H0;D1;+0:8] | null | [] | 4 | CELSIUS | 21 | HOUR | In 150 ml of THF was dissolved 11.7 g of acetyl-glycin. To this solution were added 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated under reduced pressure whereby a semi-solid substance was obtained. This substance was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | HO- | C1CCOC1 | 4 | 21 | CC(=O)NCC(=O)O.OC[C@@H]1CCCN1>C1CCOC1>CC(=O)NCC(=O)N1CCC[C@H]1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-85eb6b5c53db4d5eb20eaa4a189177c9 | CC(=O)N1CCC[C@H]1C(=O)O.OC[C@@H]1CCCN1>>CC(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C=O | C(C)(=O)N1[C@H](C(=O)O)CCC1.N1[C@H](CO)CCC1.ON1C(=O)CCC1=O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C)(=O)N1[C@H](C(=O)N2[C@H](C=O)CCC2)CCC1 | O[C:9]([C@H:8]1[N:4]([C:2]([CH3:1])=[O:3])[CH2:5][CH2:6][CH2:7]1)=[O:10].[NH:11]1[CH2:12][CH2:13][CH2:14][C@H:15]1[CH2:16][OH:17]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][C@H:15]1[CH:16]=[O:17] | CC(=O)N1CCC[C@H]1C(=O)O.OC[C@@H]1CCCN1 | CC(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C=O | null | null | C1CCOC1 | Acylation | OtherReaction | 497579ba6f41fb489dbb4af76dbcdf8e15a6e2abefa53741c204c8afba451bd0 | add54d7412d2fef46b14f8e3c2a00121d3cdce02b3129c9ad3a197b6dbfd0546 | O=C([C@@H]1CCCN1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[OH;D1;+0:10]-[CH2;D2;+0:11]-[C:12]1-[C:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[C:9]-[#7:5](-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[C:13]-[C:12]-1-[CH;D2;+0:11]=[O;H0;D1;... | null | [] | 4 | CELSIUS | 21 | HOUR | In 200 ml of THF was dissolved 15.7 g of acetyl-proline. To this solution were added under cooling with edible salt and ice 11.5 g of HOSu and 20.6 g of DCC, and the mixture was stirred for 21 hours at 4° C. The reaction liquid was filtered and the filtrate was evaporated whereby a semi-solid substance was obtained. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Secondary amine | Aldehyde.Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.C1CC[NH]C1 | HO- | C1CCOC1 | 4 | 21 | CC(=O)N1CCC[C@H]1C(=O)O.OC[C@@H]1CCCN1>C1CCOC1>CC(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-34ce3bda32144174ae81e48126bff7e2 | CC1COc2c(F)c(F)cc3c(=O)c4c(=O)[nH]oc4n1c23.CN1CCNCC1>>CC1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c4c(=O)[nH]oc4n1c23 | CC1COC2=C3N1C1=C(C(C3=CC(=C2F)F)=O)C(NO1)=O.CN1CCNCC1>>CC1COC2=C3N1C1=C(C(C3=CC(=C2N2CCN(CC2)C)F)=O)C(NO1)=O | F[c:6]1[c:5]2[c:27]3[c:17]([cH:16][c:14]1[F:15])[c:18](=[O:19])[c:20]1[c:21](=[O:22])[nH:23][o:24][c:25]1[n:26]3[CH:2]([CH3:1])[CH2:3][O:4]2.[NH:7]1[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]1>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[c:6]([N:7]3[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]3)[c:14]([F:15])[cH:16][c:17]3[c:... | CC1COc2c(F)c(F)cc3c(=O)c4c(=O)[nH]oc4n1c23.CN1CCNCC1 | CC1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c4c(=O)[nH]oc4n1c23 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | cf8dc3f90080119d981ca15fc43136c3098cf343ddfc5efa5e5536e46130b51c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]oc2c1c(=O)c1ccc(N3CCNCC3)c3c1n2CCO3 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]:[c:6]2:[#7;a:7](:[c:8]:[#8;a:9]:[#7;a:10])-[C:11]-[C:12]-[#8:13]-[c:14]:2:1.[#7:15]1-[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]-1>>[#7;a:10]:[#8;a:9]:[c:8]:[#7;a:7]1:[c:6]2:[c:5]:[c:4]:[c:2](-[F;D1;H0:3]):[c;H0;D3;+0:1](-[N;H0;D3;+0:18]3-[C:17]-[C:16]-[#7:15]-[C:20]-[C:1... | null | [] | 50 | CELSIUS | 5 | MINUTE | To a solution of 1.45 g of the preceding isoxazolo-pyrido-benzoxazine derivative (9) (R8 =CH3) in 30 ml pyridine is added in 2.5 ml N-methylpiperazine. It is then heated under nitrogen atmosphere at 50° C. for 24 hours. The mixture is evaporated to dryness and is then boiled in ethanol for 5 minutes and the mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cc2c3c(cc4cnoc4n3[CH]CO2)c1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1cc2c3c(cc4cnoc4n3[CH]CO2)c1 | C1C[NH]CC[NH]1.c1cc2c3c(cc4cnoc4n3[CH]CO2)c1 | HF | N1=CC=CC=C1 | 50 | 0.083333 | CC1COc2c(F)c(F)cc3c(=O)c4c(=O)[nH]oc4n1c23.CN1CCNCC1>N1=CC=CC=C1>CC1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c4c(=O)[nH]oc4n1c23 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8873734d8647430fb21a9471e9a9557b | C1=Cc2ccccc2ON1.O=C(OCc1ccccc1)N1CCNCC1>>O=C(OCc1ccccc1)C1=Cc2ccccc2ON1 | O1NC=CC2=C1C=CC=C2.C(=O)(OCC1=CC=CC=C1)N1CCNCC1>>C(=O)(OCC1=CC=CC=C1)C=1NOC2=C(C1)C=CC=C2 | [CH:11]1=[CH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[O:19][NH:20]1.C1CN([C:2](=[O:1])[O:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)CCN1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11]1=[CH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[O:19][NH:20]1 | C1=Cc2ccccc2ON1.O=C(OCc1ccccc1)N1CCNCC1 | O=C(OCc1ccccc1)C1=Cc2ccccc2ON1 | null | null | N1=CC=CC=C1 | C-C Coupling | OtherReaction | fd7b544a06fc9e96b9542d0a4b525df833f7bbd4be12a500a5ea3b356d7267ff | 564e4dcde845040cf4f18eb78c2d3c51660e1653c67daa4d012def6aeb4e674b | O=C(OCc1ccccc1)C1=Cc2ccccc2ON1 | [#8:1]-[#7:2]-[CH;D2;+0:3]=[C:4]-[c:5].[C:6]-[#8:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-N1-C-C-N-C-C-1>>[#8:1]-[#7:2]-[C;H0;D3;+0:3](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:7]-[C:6])=[C:4]-[c:5] | 58.1 | [{"value": 58.1, "product": "C(=O)(OCC1=CC=CC=C1)C=1NOC2=C(C1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a solution of 2.1 g of the benzoxazine (E) (R8 =CH3, R9 =C2H5, R10 =C6H5, X=F), in 30 ml pyridine is added 8 g of N-carbobenzoxypiperazine. The mixture is heated at 70° C. for 18 hours. The solvent is removed by evaporation under reduced pressure. The residue is washed with ether, water and ether. It is dried, yield... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Carbamic ester.Ether.Secondary amine | Enamine.Ester | C1=Cc2ccccc2ON1.C1CNCCN1 | C1=Cc2ccccc2ON1 | c1ccccc1.C1=Cc2ccccc2ON1 | Other | N1=CC=CC=C1 | 70 | null | C1=Cc2ccccc2ON1.O=C(OCc1ccccc1)N1CCNCC1>N1=CC=CC=C1>O=C(OCc1ccccc1)C1=Cc2ccccc2ON1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-526999a3986c46a78f6d44b277824e83 | O=C(OCc1ccccc1)N1CCNCC1.O=CNC1CCNC1>>O=C(OCc1ccccc1)C1=Cc2ccccc2ON1 | C(=O)(OCC1=CC=CC=C1)N1CCNCC1.C(=O)NC1CNCC1>>C(=O)(OCC1=CC=CC=C1)C=1NOC2=C(C1)C=CC=C2 | C1N[CH2:17][CH2:16][N:20]([C:2](=[O:1])[O:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11]1.N1[CH2:12][CH:13](N[CH:18]=[O:19])[CH2:14][CH2:15]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11]1=[CH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[O:19][NH:20]1 | O=C(OCc1ccccc1)N1CCNCC1.O=CNC1CCNC1 | O=C(OCc1ccccc1)C1=Cc2ccccc2ON1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8959c1c043f79f6b9964d79fa69e1b4928282f84a2f6381732b29401fc3f9a77 | 875982446f8a58a0e9af359625377bf402309166134e069330a71a070805ba01 | O=C(OCc1ccccc1)C1=Cc2ccccc2ON1 | [C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[N;H0;D3;+0:5]1-[CH2;D2;+0:6]-C-N-[CH2;D2;+0:7]-[CH2;D2;+0:8]-1.[O;H0;D1;+0:9]=[CH;D2;+0:10]-N-[CH;D3;+0:11]1-[CH2;D2;+0:12]-N-[CH2;D2;+0:13]-[CH2;D2;+0:14]-1>>[C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:6]1=[CH;D2;+0:12]-[c;H0;D3;+0:11]2:[cH;D2;+0:14]:[cH;D2;+0:13]:[... | null | [] | null | null | null | null | In the described fashion as Example 2(b)-2(e), replacing the N-carbobenzoxypiperazine in Example 2(e) with 3-formamidopyrrolidine, one can obtain compound (F) (R8 =CH3, R9 =C2H5, R10 =C6H5, ##STR20##
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary amide.Secondary amine.Secondary amine | Enamine.Ester | C1C[NH]CCN1.C1CCNC1 | C1=Cc2ccccc2ON1 | c1ccccc1.C1=Cc2ccccc2ON1 | Other | null | null | null | O=C(OCc1ccccc1)N1CCNCC1.O=CNC1CCNC1>>O=C(OCc1ccccc1)C1=Cc2ccccc2ON1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ff742a171fbc4d92acaa9b0b60acedc9 | C=C(C)C(=O)Cl.O=[N+]([O-])c1ccc(CO)cc1>>C=C(C)C(=O)OCc1ccc([N+](=O)[O-])cc1 | C(C(=C)C)(=O)Cl.[N+](=O)([O-])C1=CC=C(CO)C=C1>>C(C(=C)C)(=O)OCC1=CC=C(C=C1)[N+](=O)[O-] | Cl[C:4]([C:2](=[CH2:1])[CH3:3])=[O:5].[OH:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1 | C=C(C)C(=O)Cl.O=[N+]([O-])c1ccc(CO)cc1 | C=C(C)C(=O)OCc1ccc([N+](=O)[O-])cc1 | null | null | C(C)N(CC)CC | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[C;D1;H2:4])-[C;D1;H3:5].[OH;D1;+0:6]-[C:7]-[c:8]>>[C;D1;H2:4]=[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[C:7]-[c:8] | 64.6 | [{"value": 64.5, "product": "C(C(=C)C)(=O)OCC1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.6, "product": "C(C(=C)C)(=O)OCC1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | From the reaction of 52.3 g (0.5 m) methacryloyl chloride and 76.6 g (0.5 m) of p-nitrobenzyl alcohol and 50.6 g triethylamine was isolated 71.5 g (64.5%) of p-nitrobenzyl methacrylate as pale-yellow crystals, mp--87°-88° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1 | HCl | C(C)N(CC)CC | null | null | C=C(C)C(=O)Cl.O=[N+]([O-])c1ccc(CO)cc1>C(C)N(CC)CC>C=C(C)C(=O)OCc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-935ad146dc0f4ad9b7ad3ab45a8eb552 | C=CC(=O)Cl.CC(C)CC(C)O[Si](O)(OC(C)CC(C)C)OC(C)CC(C)C>>C=CC(=O)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)OC(C)CC(C)C | CC(CC(C)O[Si](O)(OC(C)CC(C)C)OC(C)CC(C)C)C.C(C)N(CC)CC.CC1=C(O)C=CC(=C1)O.C(C=C)(=O)Cl>>C(C=C)(=O)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)OC(C)CC(C)C | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[OH:5][Si:6]([O:7][CH:8]([CH3:9])[CH2:10][CH:11]([CH3:12])[CH3:13])([O:14][CH:15]([CH3:16])[CH2:17][CH:18]([CH3:19])[CH3:20])[O:21][CH:22]([CH3:23])[CH2:24][CH:25]([CH3:26])[CH3:27]>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][Si:6]([O:7][CH:8]([CH3:9])[CH2:10][CH:11]([CH3:12])[CH3:13])([O:14][CH:15]... | C=CC(=O)Cl.CC(C)CC(C)O[Si](O)(OC(C)CC(C)C)OC(C)CC(C)C | C=CC(=O)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)OC(C)CC(C)C | null | null | C1(=CC=CC=C1)C | Acylation | Schotten-Baumann to ester | 179ae8baa325b2dace7c965a68a4b2b7e91bea49291f7cdbcd29e5947f465078 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C:5]-[C:6](-[C;D1;H3:7])-[#8:8]-[#14:9](-[OH;D1;+0:10])(-[#8:11]-[C:12](-[C:13])-[C;D1;H3:14])-[#8:15]-[C:16](-[C:17])-[C;D1;H3:18]>>[C:5]-[C:6](-[C;D1;H3:7])-[#8:8]-[#14:9](-[#8:11]-[C:12](-[C:13])-[C;D1;H3:14])(-[#8:15]-[C:16](-[C:17])-[C;D1;H3:18])-[O;H0;D2;+0:10]-[... | null | [] | 5 | CELSIUS | 0.5 | HOUR | 0.23 moles of tris(4-methyl-2pentoxy)silanol, 0.23 moles of triethylamine, 0.02 gms. of methyl hydroquinone as polymerization inhibitor and 82 cc of toluene were placed in a three necked flask equipped with a stirrer, addition funnel, a thermometer and a condenser. A solution of 0.23 moles of acryloyl chloride in 23 cc... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | null | HCl | C1(=CC=CC=C1)C | 5 | 0.5 | C=CC(=O)Cl.CC(C)CC(C)O[Si](O)(OC(C)CC(C)C)OC(C)CC(C)C>C1(=CC=CC=C1)C>C=CC(=O)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)OC(C)CC(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9c1df3ee32c648c6ad9f27cffc07722b | C1=CC2C3C=CC(C3)C2C1.O=C1C=CC(=O)O1>>O=C1OC(=O)C2=C1C1CCC2C1 | B(F)(F)F.CCOCC.C1=CC=CC1.C1C=CC2C1C3CC2C=C3.C1(\C=C/C(=O)O1)=O.C1=CC=CC1.C1(\C=C/C(=O)O1)=O.C1=CC=CC1>>C12C3=C(C(CC1)C2)C(=O)OC3=O | C1=CC2C(C1)[CH:11]1[CH:10]=[CH:9][CH:8]2[CH2:12]1.[O:1]=[C:2]1[O:3][C:4](=[O:5])[CH:6]=[CH:7]1>>[O:1]=[C:2]1[O:3][C:4](=[O:5])[C:6]2=[C:7]1[CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12]1 | C1=CC2C3C=CC(C3)C2C1.O=C1C=CC(=O)O1 | O=C1OC(=O)C2=C1C1CCC2C1 | null | null | null | C-C Coupling | OtherReaction | 0658762f0c8a0e3589f449bf8e8f0fdb20e14d6466d297bbcc93cde18498374c | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1OC(=O)C2=C1C1CCC2C1 | C1-C=C-C2-C-1-[CH;D3;+0:1]1-[C:2]-[CH;D3;+0:3]-2-[CH;D2;+0:4]=[CH;D2;+0:5]-1.[O;D1;H0:6]=[C:7]1-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[CH;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D3;+0:11]2=[C;H0;D3;+0:12]-1-[CH;D3;+0:3]1-[C:2]-[CH;D3;+0:1]-2-[CH2;D2;+0:5]-[CH2;D2;+0:4]-1 | null | [] | 100 | CELSIUS | null | null | Mixed polybasic anhydride containing a plurality of 1,2 anhydrides is obtained by distilling, at 200° C., 66.10 gms. (1 mole) of cyclopentadiene directly from dicyclopentadiene into a reactor containing 98.06 gms. (1 mole) of maleic anhydride, heated to a temperature of 55° C. When the transfer is complete, the reactio... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC2C3C=CC(C3)C2C1.C1=CCOC1 | C1OCC2=C1C1CCC2C1 | C1OCC2=C1C1CCC2C1 | Other | null | 100 | null | C1=CC2C3C=CC(C3)C2C1.O=C1C=CC(=O)O1>>O=C1OC(=O)C2=C1C1CCC2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f40a936c94c845e5b7427cc43a48bbc2 | ClCc1cccc2c1CC2.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>C1=Cc2cc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)ccc21.[Cl-] | ClCC1=C2C(CC2)=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)OCC>>[Cl-].C1(=CC=CC=C1)[P+](CC1=CC2=C(C=C2)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH2:1]1[CH2:2][c:3]2[c:4]1[c:5]([CH2:6][Cl:29])[cH:26][cH:27][cH:28]2.[P:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH:1]1=[CH:2][c:3]2[cH:4][c:5]([CH2:6][P+:7]([c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)([c:14]3[cH:15][cH:16][... | ClCc1cccc2c1CC2.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | C1=Cc2cc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)ccc21.[Cl-] | null | null | C(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 127f8013fd832f07dba9c227580ae1d03fe917a64b25bf9f7f4f72f6647c370e | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | C1=Cc2cc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)ccc21 | [Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]2:[c;H0;D3;+0:8]:1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-2.[c:11]:[c:12](-[P;H0;D3;+0:13](-[c:14](:[c:15]):[c:16])-[c:17](:[c:18]):[c:19]):[c:20]>>[Cl-;H0;D0:1].[c:11]:[c:12](-[P+;H0;D4:13](-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6]2:[c:7](:[cH;D2;+0:8]:1)... | null | [] | null | null | null | null | A solution of 4-chloromethylbenzocyclobutene (24.4 g, 160 mmol) and triphenylphosphine (41.9 g, 160 mmol) in 120 ml of chloroform was heated at reflux for 24 h. Addition of diethyl ether followed by filtration gave tripheny(4-benzocyclobutenyl)methyl phosphonium chloride as a white powder: 1H NMR (CDCl3) δ 3.03 (m,4H),... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)CC2 | C1=Cc2ccccc21 | C1=Cc2ccccc21.c1ccccc1.c1ccccc1.c1ccccc1 | null | C(Cl)(Cl)Cl | null | null | ClCc1cccc2c1CC2.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(Cl)(Cl)Cl>C1=Cc2cc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)ccc21.[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cf5545f16dea40129101d2f1afd58139 | CCOC(=O)c1cccc2c1C(=O)NC2=O.N[C@@H](CCC(=O)O)C(=O)O>>O=C(O)CC[C@@H](C(=O)O)N1C(=O)c2ccccc2C1=O | N[C@@H](CCC(=O)O)C(=O)O.C(=O)(OCC)C1=C2C(C(=O)NC2=O)=CC=C1.Cl>>C1=CC=C2C(=C1)C(=O)N(C2=O)[C@@H](CCC(=O)O)C(=O)O | CCOC(=O)[c:17]1[cH:16][cH:15][cH:14][c:13]2[c:18]1[C:19](=[O:20])N[C:11]2=[O:12].[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C@@H:6]([C:7](=[O:8])[OH:9])[NH2:10]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C@@H:6]([C:7](=[O:8])[OH:9])[N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]1=[O:20] | CCOC(=O)c1cccc2c1C(=O)NC2=O.N[C@@H](CCC(=O)O)C(=O)O | O=C(O)CC[C@@H](C(=O)O)N1C(=O)c2ccccc2C1=O | null | null | O.C(=O)([O-])[O-].[Na+].[Na+] | Acylation | OtherReaction | 2b45f6b619eb8bd9d4bc08669ad59bb1350f0f4b700005a96469668ff7f0a752 | f5beba068e800ae7c821e0ef927c2c1ed8bb38603152d4afd976f5e5536c9939 | O=C1NC(=O)c2ccccc21 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[c:6]:1-[C;H0;D3;+0:7](=[O;D1;H0:8])-N-[C;H0;D3;+0:9]-2=[O;D1;H0:10].[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]>>[C:11]-[C:12](-[C:14](=[O;D1;H0:15])-[O;D1;H1:16])-[N;H0;D3;+0:13]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:5]2:[c:4]:[c:3]:[c:2]:[cH;D2;+... | null | [] | null | null | null | null | In a solution of Na2CO3 (51.5 g) in water (350 ml) at 5° C. was dissolved L-glutamic acid (29.4 g). Carboethoxy phthalimide (59.6 g) was added to the solution and suspended therein and thereafter reacted at 350° C. for 30-40 minutes. Then the solution was freed from insoluble matter, adjusted to pH 2.5 with 6N-HCl, and... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Unsubstituted dicarboximide.Primary amine | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | O.C(=O)([O-])[O-].[Na+].[Na+] | null | null | CCOC(=O)c1cccc2c1C(=O)NC2=O.N[C@@H](CCC(=O)O)C(=O)O>O.C(=O)([O-])[O-].[Na+].[Na+]>O=C(O)CC[C@@H](C(=O)O)N1C(=O)c2ccccc2C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e332db8ef9054b4da65d31751cd05d4e | NCCC(=O)O.O=C1OC(=O)c2ccccc21>>O=C(O)CCN1C(=O)c2ccccc2C1=O | C1(C=2C(C(=O)O1)=CC=CC2)=O.NCCC(=O)O>>C1=CC=C2C(=C1)C(=O)N(C2=O)CCC(=O)O | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][NH2:6].O1[C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][N:6]1[C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16] | NCCC(=O)O.O=C1OC(=O)c2ccccc21 | O=C(O)CCN1C(=O)c2ccccc2C1=O | null | null | O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [NH2;D1;+0:1]-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[O;D1;H0:7]=[C;H0;D3;+0:8]1-[N;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14] | null | [] | 200 | CELSIUS | null | null | A mixture of phthalic anhydride (500 g) and β-alanine (267 g) was fused by heating at 200° C. for 15 minutes, and poured into water (1500 ml). The formed precipitate was collected by filtration, and recrystallized from ethanol to give phthaloyl-β-alanine (hereinafter referred to as pht-βAla), yield 537 g, 81.6%.
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | O | 200 | null | NCCC(=O)O.O=C1OC(=O)c2ccccc21>O>O=C(O)CCN1C(=O)c2ccccc2C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6914315e228943eeb39582f4465b51a9 | CC(=O)O.Nc1ncccc1CO.Sc1nc2ccccc2[nH]1>>Nc1ncccc1CSc1nc2ccccc2[nH]1.Nc1ncccc1CSc1nc2ccccc2[nH]1.O | C([O-])([O-])=O.[K+].[K+].SC=1NC2=C(N1)C=CC=C2.OCC=1C(=NC=CC1)N.C(C)(=O)O>>O.N1C(=NC2=C1C=CC=C2)SCC=2C(=NC=CC2)N.N2C(=NC1=C2C=CC=C1)SCC=1C(=NC=CC1)N | O=[C:33](O)[CH3:34].[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][OH:37].[SH:9][c:10]1[n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[nH:18]1>>[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][S:9][c:10]1[n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[nH:18]1.[NH2:19][c:20]1[n:21][cH:22][cH:23][cH:24][c:25]1[CH2:... | CC(=O)O.Nc1ncccc1CO.Sc1nc2ccccc2[nH]1 | Nc1ncccc1CSc1nc2ccccc2[nH]1.Nc1ncccc1CSc1nc2ccccc2[nH]1.O | null | null | O.Br | Aromatic Heterocycle Formation | OtherReaction | 08710f04c0a079ce667b34bcbb357f003081afe12ff3d21e69d810848f6af717 | 623b43da0787b6bf180f91057c90ed558797673ab16de5018519d3405e9ce0f8 | c1cncc(CSc2nc3ccccc3[nH]2)c1.c1cncc(CSc2nc3ccccc3[nH]2)c1 | O-[C;H0;D3;+0:1](=O)-[CH3;D1;+0:2].[N;D1;H2:3]-[c:4](:[#7;a:5]:[c:6]):[c:7](-[CH2;D2;+0:8]-[OH;D1;+0:9]):[c:10].[SH;D1;+0:11]-[c:12]1:[#7;a:13]:[c:14]:[c:15]:[#7;a:16]:1>>[#7;a:17]:[c:18]1:[c:19]:[c:20]:[c:21]:[cH;D2;+0:1]:[cH;D2;+0:2]:1.[N;D1;H2:3]-[c:4](:[#7;a:5]:[c:6]):[c:7](-[CH2;D2;+0:8]-[S;H0;D2;+0:11]-[c:12]1:[#... | null | [] | null | null | null | null | A mixture of 9.6 g (63 mmole) of 2-mercaptobenzimidazole and 7.7 g (62 mmole) of 3-hydroxymethyl-2-pyridinamine was dissolved in 60 ml of 48% aqueous hydrobromic acid and 60 ml of acetic acid and heated to reflux. After being cooled to room temperature, the mixture was poured into water and make alkaline with potassium... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Aromatic thiol | Primary amine.Monosulfide.Monosulfide | null | c1ccncc1.c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1.c1ccncc1.c1ccc2[nH]cnc2c1 | null | O.Br | null | null | CC(=O)O.Nc1ncccc1CO.Sc1nc2ccccc2[nH]1>O.Br>Nc1ncccc1CSc1nc2ccccc2[nH]1.Nc1ncccc1CSc1nc2ccccc2[nH]1.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0be0315eef2a4e0bbe52f53f5fca31f4 | Nc1ncccc1CSc1nc2ccccc2[nH]1>>c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | O.N1C(=NC2=C1C=CC=C2)SCC=2C(=NC=CC2)N.N2C(=NC1=C2C=CC=C1)SCC=1C(=NC=CC1)N.ClCC=O.C([O-])(O)=O.[Na+]>>N=1C=CN2C1C(=CC=C2)CSC2=NC1=C(N2)C=CC=C1 | [cH:1]1[cH:2][cH:3][c:4]2[nH:5][c:6]([S:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][n:13][c:17]3[NH2:16])[n:18][c:19]2[cH:20]1>>[cH:1]1[cH:2][cH:3][c:4]2[nH:5][c:6]([S:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][n:13]4[cH:14][cH:15][n:16][c:17]34)[n:18][c:19]2[cH:20]1 | Nc1ncccc1CSc1nc2ccccc2[nH]1 | c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 6d486165009112780e608dff97176824bff10b35baa5286e796a3ea4a90aee71 | 0c2e6cfe0bdb8f8cd78303a7637b3ef339f807f5bc27c4a22ad516ce20b37476 | c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5]:[c:6]>>[c:6]:[c:5]:[n;H0;D3;+0:4]1:[c:7]:[c:8]:[n;H0;D2;+0:1]:[c:2]:1:[c:3] | 71.3 | [{"value": 71.3, "product": "N=1C=CN2C1C(=CC=C2)CSC2=NC1=C(N2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 9.6 g (63 mmole) of 2-mercaptobenzimidazole and 7.7 g (62 mmole) of 3-hydroxymethyl-2-pyridinamine was dissolved in 60 ml of 48% aqueous hydrobromic acid and 60 ml of acetic acid and heated to reflux. After being cooled to room temperature, the mixture was poured into water and make alkaline with potassium... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | Other | C(C)O | null | null | Nc1ncccc1CSc1nc2ccccc2[nH]1>C(C)O>c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b30781462e834610ab3fc2e2c3d31c48 | CC(=O)CBr.Nc1ncccc1CSc1nc2ccccc2[nH]1>>Cc1cn2cccc(CSc3nc4ccccc4[nH]3)c2n1 | O.N1C(=NC2=C1C=CC=C2)SCC=2C(=NC=CC2)N.N2C(=NC1=C2C=CC=C1)SCC=1C(=NC=CC1)N.BrCC(C)=O.C([O-])(O)=O.[Na+]>>CC=1N=C2N(C=CC=C2CSC2=NC3=C(N2)C=CC=C3)C1 | O=[C:2]([CH3:1])[CH2:3]Br.[n:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][S:10][c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[nH:19]2)[c:20]1[NH2:21]>>[CH3:1][c:2]1[cH:3][n:4]2[cH:5][cH:6][cH:7][c:8]([CH2:9][S:10][c:11]3[n:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[nH:19]3)[c:20]2[n:21]1 | CC(=O)CBr.Nc1ncccc1CSc1nc2ccccc2[nH]1 | Cc1cn2cccc(CSc3nc4ccccc4[nH]3)c2n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C;D1;H3:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[n;H0;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](:[c:6]):[n;H0;D2;+0:4]:1 | 36.2 | [{"value": 36.2, "product": "CC=1N=C2N(C=CC=C2CSC2=NC3=C(N2)C=CC=C3)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3.8 g (15 mmole) of 3-[(1H-benzimidazol-2-ylthio)methyl]-2-pyridinamine hemihydrate (see Example 1), 2.4 g (18 mmole) of bromoacetone, and 2.1 g (25 mmole) of sodium bicarbonate in 50 ml of ethanol was stirred at room temperature. After 18 hours the mixture was concentrated in vacuo to a residue that was p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccc2[nH]cnc2c1 | HBr | C(C)O | null | null | CC(=O)CBr.Nc1ncccc1CSc1nc2ccccc2[nH]1>C(C)O>Cc1cn2cccc(CSc3nc4ccccc4[nH]3)c2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4380a12b563c4abdbd36dc933a51f2b0 | Nc1ncccc1CO>>OCc1cccn2ccnc12 | OCC=1C(=NC=CC1)N.ClCC=O.C([O-])(O)=O.[Na+]>>OCC=1C=2N(C=CC1)C=CN2 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:11]1[NH2:10]>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7]2[cH:8][cH:9][n:10][c:11]12 | Nc1ncccc1CO | OCc1cccn2ccnc12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 6d486165009112780e608dff97176824bff10b35baa5286e796a3ea4a90aee71 | 0c2e6cfe0bdb8f8cd78303a7637b3ef339f807f5bc27c4a22ad516ce20b37476 | c1ccn2ccnc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5]:[c:6]>>[c:3]:[c:2]1:[n;H0;D2;+0:1]:[c:7]:[c:8]:[n;H0;D3;+0:4]:1:[c:5]:[c:6] | 129.1 | [{"value": 129.1, "product": "OCC=1C=2N(C=CC1)C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2.92 g (23 mmole) of 3-hydroxymethyl-2-pyridinamine, 6.15 g (35 mmole) of chloroacetaldehyde, and 2.0 g (35 mmole) of sodium bicarbonate in 100 ml of ethanol was heated at reflux for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to a solid. Recrystallization from diethyl et... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | Other | C(C)O | null | null | Nc1ncccc1CO>C(C)O>OCc1cccn2ccnc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fa237b32af6b4b098a33a40beb816430 | COc1ccc2nc(S)[nH]c2c1.OCc1cccn2ccnc12>>COc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | SC=1NC2=C(N1)C=CC(=C2)OC.OCC=1C=2N(C=CC1)C=CN2>>N=1C=CN2C1C(=CC=C2)CSC2=NC1=C(N2)C=CC(=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([SH:9])[nH:20][c:21]2[cH:22]1.O[CH2:10][c:11]1[cH:12][cH:13][cH:14][n:15]2[cH:16][cH:17][n:18][c:19]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([S:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][n:15]4[cH:16][cH:17][n:18][c:19]34)[n:20][c:21]2[cH:22]1 | COc1ccc2nc(S)[nH]c2c1.OCc1cccn2ccnc12 | COc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | null | null | C(C)(=O)O.Br | Heteroatom Alkylation and Arylation | OtherReaction | c119424abb7b621e5fb126e8156c5e4310815e8f2d609f48f2eb427b327d29ac | c1ccf05c97341d9cf75acae4c03f7d5a8212340a35905af6c8d60b4ccc775d1f | c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:9].[SH;D1;+0:10]-[c:11]1:[n;H0;D2;+0:12]:[c:13](:[c:14]):[c:15](:[c:16]):[nH;D2;+0:17]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[c:11]1:[n;H0;D2;+0:17]:[c:15](:[c:16]):[c:13](:[c:14]):[nH;D2;+0:12]:1):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:... | null | [] | null | null | null | null | A mixture of 2.92 g (23 mmole) of 3-hydroxymethyl-2-pyridinamine, 6.15 g (35 mmole) of chloroacetaldehyde, and 2.0 g (35 mmole) of sodium bicarbonate in 100 ml of ethanol was heated at reflux for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to a solid. Recrystallization from diethyl et... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | HO- | C(C)(=O)O.Br | null | null | COc1ccc2nc(S)[nH]c2c1.OCc1cccn2ccnc12>C(C)(=O)O.Br>COc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3c20324bed6f42eb896131d2c2e708b2 | Cc1cccc([N+](=O)[O-])c1N>>Cc1cccc2nc(S)[nH]c12 | [OH-].[K+].CC1=C(N)C(=CC=C1)[N+](=O)[O-].C(C)OC(=S)[S-].[K+].[H][H]>>SC=1NC2=C(N1)C=CC=C2C | O=[N+:7]([O-])[c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:11]1[NH2:10]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[n:7][c:8]([SH:9])[nH:10][c:11]12 | Cc1cccc([N+](=O)[O-])c1N | Cc1cccc2nc(S)[nH]c12 | null | [Pd] | O.Cl.CO.O1CCCC1.C(C)O | Aromatic Heterocycle Formation | OtherReaction | c2c29974f4b5be07c21486a5b198dab3d77dbe80b212fcca89a8c66a9fb55acd | ecf3fe2b0af561b8897dfd28d098c701162f656ce0345b917de68408521bab59 | c1ccc2[nH]cnc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6]>>[S;D1;H1:7]-[c:8]1:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:6]):[nH;D2;+0:5]:1 | 29 | [{"value": 29.0, "product": "SC=1NC2=C(N1)C=CC=C2C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 20 g (0.13 mole) of 2-methyl-6-nitroaniline in 22.9 ml of concentrated aqueous hydrochloric acid, 200 ml of tetrahydrofuran, and 350 ml of methanol was hydrogenated at room temperature using 25 p.s.i. of hydrogen gas over 2.0 g of 5% palladium on carbon. The mixture was filtered and the filtrate was conce... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary amine | Aromatic thiol | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | null | [Pd].O.Cl.CO.O1CCCC1.C(C)O | null | null | Cc1cccc([N+](=O)[O-])c1N>[Pd].O.Cl.CO.O1CCCC1.C(C)O>Cc1cccc2nc(S)[nH]c12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b748a2da9da44030b2c8933dceb77443 | Cc1cccc2nc(S)[nH]c12.OCc1cccn2ccnc12>>Cc1cccc2[nH]c(SCc3cccn4ccnc34)nc12 | OCC=1C=2N(C=CC1)C=CN2.SC=1NC2=C(N1)C=CC=C2C>>N=1C=CN2C1C(=CC=C2)CSC2=NC1=C(N2)C=CC=C1C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[n:7][c:8]([SH:9])[nH:20][c:21]12.O[CH2:10][c:11]1[cH:12][cH:13][cH:14][n:15]2[cH:16][cH:17][n:18][c:19]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][c:8]([S:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][n:15]4[cH:16][cH:17][n:18][c:19]34)[n:20][c:21]12 | Cc1cccc2nc(S)[nH]c12.OCc1cccn2ccnc12 | Cc1cccc2[nH]c(SCc3cccn4ccnc34)nc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c119424abb7b621e5fb126e8156c5e4310815e8f2d609f48f2eb427b327d29ac | c1ccf05c97341d9cf75acae4c03f7d5a8212340a35905af6c8d60b4ccc775d1f | c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:9].[SH;D1;+0:10]-[c:11]1:[n;H0;D2;+0:12]:[c:13](:[c:14]):[c:15](:[c:16]):[nH;D2;+0:17]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[c:11]1:[n;H0;D2;+0:17]:[c:15](:[c:16]):[c:13](:[c:14]):[nH;D2;+0:12]:1):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:... | null | [] | null | null | null | null | A solution of 20 g (0.13 mole) of 2-methyl-6-nitroaniline in 22.9 ml of concentrated aqueous hydrochloric acid, 200 ml of tetrahydrofuran, and 350 ml of methanol was hydrogenated at room temperature using 25 p.s.i. of hydrogen gas over 2.0 g of 5% palladium on carbon. The mixture was filtered and the filtrate was conce... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cccc2nc(S)[nH]c12.OCc1cccn2ccnc12>>Cc1cccc2[nH]c(SCc3cccn4ccnc34)nc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a6c6686884974bc0978bd9d303374472 | Cc1ccc(N)c(N)c1.S=C=S>>Cc1ccc2nc(S)[nH]c2c1 | NC=1C=C(C=CC1N)C.C(=S)=S.[OH-].[Na+]>>SC=1NC2=C(N1)C=CC(=C2)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:10]([NH2:9])[cH:11]1.S=[C:7]=[S:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([SH:8])[nH:9][c:10]2[cH:11]1 | Cc1ccc(N)c(N)c1.S=C=S | Cc1ccc2nc(S)[nH]c2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 2f9e8f971ef311f12ade4ccd0b4deb85651fd2c86b2382ec0e197ea3688b92b0 | 18fba499a006bfcf84ddf6a88a094e67137a08753094717f44b09456e676cee0 | c1ccc2[nH]cnc2c1 | S=[C;H0;D2;+0:1]=[S;H0;D1;+0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[NH2;D1;+0:7]):[c:8]>>[SH;D1;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:8]):[nH;D2;+0:7]:1 | null | [] | null | null | null | null | A mixture of 12.2 g (0.1 mole) of 3,4-diaminotoluene, 35 ml of carbon disulfide, and 4.0 g (0.1 mole) of sodium hydroxide was heated at reflux in 350 ml of ethanol. After 2.5 hours the mixture was concentrated in vacuo. The residue was suspended in 200 ml of 4% aqueous hydrochloric acid, collected by filtration, washed... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Aromatic thiol | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | Other | C(C)O | null | null | Cc1ccc(N)c(N)c1.S=C=S>C(C)O>Cc1ccc2nc(S)[nH]c2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e6c84d7e8b524308ae06567cb35cd1c2 | Cc1ccc2nc(S)[nH]c2c1.OCc1cccn2ccnc12>>Cc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1.Cc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1.O | OCC=1C=2N(C=CC1)C=CN2.SC=1NC2=C(N1)C=CC(=C2)C>>O.N=1C=CN2C1C(=CC=C2)CSC2=NC1=C(N2)C=CC(=C1)C.N=1C=CN2C1C(=CC=C2)CSC2=NC1=C(N2)C=CC(=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([SH:8])[nH:19][c:20]2[cH:21]1.[CH2:9]([c:10]1[c:18]2[n:17][cH:16][cH:15][n:35]2[cH:34][cH:33][cH:32]1)[OH:43]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7]([S:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]4[cH:15][cH:16][n:17][c:18]34)[n:19][c:20]2[cH:21]1.[CH3:22][c:23]1[cH:24][cH:... | Cc1ccc2nc(S)[nH]c2c1.OCc1cccn2ccnc12 | Cc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1.Cc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1.O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 71770e1bb66ee2befa0d96f0957ce88df9527e1e788f09af8d3ea277e1c907f2 | ee37368c7917e89132d85116d4cbd6798e6e21e6544198f158bb89e3e9055da9 | c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1.c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:5]:[c:6]:[n;H0;D3;+0:7]2:[cH;D2;+0:8]:[c:9]:[#7;a:10]:[c;H0;D3;+0:11]:1:2.[SH;D1;+0:12]-[c:13]1:[n;H0;D2;+0:14]:[c:15](:[c:16]):[c:17](:[c:18]):[nH;D2;+0:19]:1>>[C:20]-[c:21]1:[cH;D2;+0:4]:[c:5]:[c:6]:[n;H0;D3;+0:7]2:[c:22]:[c:23]:[#7;a:24]:[c:25]:1:2.[OH2;D0;+... | null | [] | null | null | null | null | A mixture of 12.2 g (0.1 mole) of 3,4-diaminotoluene, 35 ml of carbon disulfide, and 4.0 g (0.1 mole) of sodium hydroxide was heated at reflux in 350 ml of ethanol. After 2.5 hours the mixture was concentrated in vacuo. The residue was suspended in 200 ml of 4% aqueous hydrochloric acid, collected by filtration, washed... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide.Monosulfide | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1.c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | Other | null | null | null | Cc1ccc2nc(S)[nH]c2c1.OCc1cccn2ccnc12>>Cc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1.Cc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-25a1f3abfbc44119b668313011b4e3e4 | Cc1cc(N)c(N)cc1C>>Cc1cc2nc(S)[nH]c2cc1C | CC1=CC(=C(C=C1C)N)N.C(C)OC(=S)[S-].[K+]>>CC1=CC2=C(N=C(N2)S)C=C1C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:9]([NH2:8])[cH:10][c:11]1[CH3:12]>>[CH3:1][c:2]1[cH:3][c:4]2[n:5][c:6]([SH:7])[nH:8][c:9]2[cH:10][c:11]1[CH3:12] | Cc1cc(N)c(N)cc1C | Cc1cc2nc(S)[nH]c2cc1C | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2f9e8f971ef311f12ade4ccd0b4deb85651fd2c86b2382ec0e197ea3688b92b0 | 18fba499a006bfcf84ddf6a88a094e67137a08753094717f44b09456e676cee0 | c1ccc2[nH]cnc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6]>>[S;D1;H1:7]-[c:8]1:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:6]):[nH;D2;+0:5]:1 | null | [] | null | null | null | null | Reaction of 30 g (0.22 mole) of 4,5-dimethyl-1,2-phenylenediamine with potassium ethylxanthate using the method described in Example 10 yielded 19 g of 5,6-dimethyl-2-mercaptobenzimidazole, as confirmed by the nmr and infrared spectra and by elemental analysis. The title compound (591 mg) was prepared by the method of ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Aromatic thiol | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | Other | null | null | null | Cc1cc(N)c(N)cc1C>>Cc1cc2nc(S)[nH]c2cc1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1cf71a1c5fb448e3a1a4c042114e077e | OCc1cccn2ccnc12.Sc1nc2ccc(Cl)cc2[nH]1>>Clc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | OCC=1C=2N(C=CC1)C=CN2.ClC1=CC2=C(N=C(N2)S)C=C1>>ClC1=CC2=C(NC(=N2)SCC=2C=3N(C=CC2)C=CN3)C=C1 | O[CH2:9][c:10]1[cH:11][cH:12][cH:13][n:14]2[cH:15][cH:16][n:17][c:18]12.[Cl:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([SH:8])[nH:19][c:20]2[cH:21]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7]([S:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]4[cH:15][cH:16][n:17][c:18]34)[n:19][c:20]2[cH:21]1 | OCc1cccn2ccnc12.Sc1nc2ccc(Cl)cc2[nH]1 | Clc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c119424abb7b621e5fb126e8156c5e4310815e8f2d609f48f2eb427b327d29ac | c1ccf05c97341d9cf75acae4c03f7d5a8212340a35905af6c8d60b4ccc775d1f | c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:9].[SH;D1;+0:10]-[c:11]1:[n;H0;D2;+0:12]:[c:13](:[c:14]):[c:15](:[c:16]):[nH;D2;+0:17]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[c:11]1:[n;H0;D2;+0:17]:[c:15](:[c:16]):[c:13](:[c:14]):[nH;D2;+0:12]:1):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:... | null | [] | null | null | null | null | A solution of 20 g (0.12 mole) of 3-chloro-6-nitroaniline in 350 ml of methanol was hydrogenated over 5% palladium on carbon to yield 24.9 g of the corresponding diamino compound. Reaction of the diamino compound with potassium ethylxanthate using the method described in Example 10 yielded 19 g of 5-chloro-2-mercaptobe... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | HO- | null | null | null | OCc1cccn2ccnc12.Sc1nc2ccc(Cl)cc2[nH]1>>Clc1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-eff051348c4b450b8fe17199751685fc | CC(=O)C(C)Cl.CC(=O)OCc1cccnc1N>>CC(=O)OCc1cccn2c(C)c(C)nc12 | C(C)(=O)OCC=1C(=NC=CC1)N.ClC(C(C)=O)C.[I-].[K+]>>C(C)(=O)OCC=1C=2N(C=CC1)C(=C(N2)C)C | O=[C:11]([CH3:12])[CH:13](Cl)[CH3:14].[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10][c:16]1[NH2:15]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10]2[c:11]([CH3:12])[c:13]([CH3:14])[n:15][c:16]12 | CC(=O)C(C)Cl.CC(=O)OCc1cccnc1N | CC(=O)OCc1cccn2c(C)c(C)nc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 68f76555483972bc3db5d3d4b5e479a66c1f89ab1b71b2a0fb941126aa9c191a | 235fd48cd394ba1137abde2ba7484c051be6ffcae187060d6065fe5adf0e90a3 | c1ccn2ccnc2c1 | Cl-[CH;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=O)-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D2;+0:5]:[c:6](:[c:7]):[n;H0;D3;+0:8]:1:[c:9]:[c:10] | 28.2 | [{"value": 28.2, "product": "C(C)(=O)OCC=1C=2N(C=CC1)C(=C(N2)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2.0 g (12 mmole) of 3-(acetoxymethyl)-2-pyridinamine, 1.7 g (17 mmole) of 3-chloro-2-butanone, and one crystal of potassium iodide was heated at 100° for 4.5 hours. The mixture was allowed to cool and was partitioned between aqueous potassium carbonate and dichloromethane. The organic phase was separated, ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HCl | null | null | null | CC(=O)C(C)Cl.CC(=O)OCc1cccnc1N>>CC(=O)OCc1cccn2c(C)c(C)nc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-747991975c614cf3ace7cd83f57b627a | CC(=O)OCc1cccn2c(C)c(C)nc12.Sc1nc2ccccc2[nH]1>>Cc1nc2c(CSc3nc4ccccc4[nH]3)cccn2c1C | C(C)(=O)OCC=1C=2N(C=CC1)C(=C(N2)C)C.SC=1NC2=C(N1)C=CC=C2>>CC=1N=C2N(C=CC=C2CSC2=NC3=C(N2)C=CC=C3)C1C | CC(=O)O[CH2:6][c:5]1[c:4]2[n:3][c:2]([CH3:1])[c:21]([CH3:22])[n:20]2[cH:19][cH:18][cH:17]1.[SH:7][c:8]1[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[nH:16]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([CH2:6][S:7][c:8]3[n:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[nH:16]3)[cH:17][cH:18][cH:19][n:20]2[c:21]1[CH3:22] | CC(=O)OCc1cccn2c(C)c(C)nc12.Sc1nc2ccccc2[nH]1 | Cc1nc2c(CSc3nc4ccccc4[nH]3)cccn2c1C | null | null | C(C)(=O)O.Br | Heteroatom Alkylation and Arylation | OtherReaction | a6a1a19cf663515a44b0f453ada37e5a4daffb7fa3d960443c6193f945fe684c | c1c742f57df6accfc044260f03f42fd14bb3b3abd9eed9176ff83ab0921ba9e6 | c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | C-C(=O)-O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:9].[SH;D1;+0:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]:1):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:9] | 106.4 | [{"value": 106.4, "product": "CC=1N=C2N(C=CC=C2CSC2=NC3=C(N2)C=CC=C3)C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2.0 g (12 mmole) of 3-(acetoxymethyl)-2-pyridinamine, 1.7 g (17 mmole) of 3-chloro-2-butanone, and one crystal of potassium iodide was heated at 100° for 4.5 hours. The mixture was allowed to cool and was partitioned between aqueous potassium carbonate and dichloromethane. The organic phase was separated, ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic thiol | Monosulfide | null | null | c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | HO- | C(C)(=O)O.Br | null | null | CC(=O)OCc1cccn2c(C)c(C)nc12.Sc1nc2ccccc2[nH]1>C(C)(=O)O.Br>Cc1nc2c(CSc3nc4ccccc4[nH]3)cccn2c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1d40358b53004bc19e0580dfc4e6614b | CC(=O)OCc1cccnc1N.CC(Br)C=O>>CC(=O)OCc1cccn2c(C)cnc12 | C(C)(=O)OCC=1C(=NC=CC1)N.BrC(C=O)C>>C(C)(=O)OCC=1C=2N(C=CC1)C(=CN2)C | [CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10][c:15]1[NH2:14].O=[CH:13][CH:11](Br)[CH3:12]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10]2[c:11]([CH3:12])[cH:13][n:14][c:15]12 | CC(=O)OCc1cccnc1N.CC(Br)C=O | CC(=O)OCc1cccn2c(C)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3a7835efa5ac56b87be43234b54606ae621fc957a5ff407573e590f6174c2545 | 4efe5597cd78b75eedda88a299158b349ae1f03c7cd5a6a1daf8cec0515aae7c | c1ccn2ccnc2c1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[CH;D2;+0:3]=O.[NH2;D1;+0:4]-[c:5](:[c:6]):[n;H0;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[c:5](:[c:6]):[n;H0;D3;+0:7]:1:[c:8]:[c:9] | 37.5 | [{"value": 37.5, "product": "C(C)(=O)OCC=1C=2N(C=CC1)C(=CN2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5.0 g (30 mmole) of 3-(acetoxymethyl)-2-pyridinamine and 4.8 g (35 mmole) of 2-bromopropanal spontaneously heated upon mixing. After cooling, the mixture was partitioned between aqueous potassium carbonate and dichloromethane. The organic phase was separated, washed with water, dried over magnesium sulfate... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | null | null | null | CC(=O)OCc1cccnc1N.CC(Br)C=O>>CC(=O)OCc1cccn2c(C)cnc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-53c734d52032499ab6a88264f406cab5 | CC(=O)OCc1cccn2c(C)cnc12.Sc1nc2ccccc2[nH]1>>Cc1cnc2c(CSc3nc4ccccc4[nH]3)cccn12 | C(C)(=O)OCC=1C=2N(C=CC1)C(=CN2)C.SC=1NC2=C(N1)C=CC=C2>>CC1=CN=C2N1C=CC=C2CSC2=NC1=C(N2)C=CC=C1 | CC(=O)O[CH2:7][c:6]1[c:5]2[n:4][cH:3][c:2]([CH3:1])[n:21]2[cH:20][cH:19][cH:18]1.[SH:8][c:9]1[n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[nH:17]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([CH2:7][S:8][c:9]3[n:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[nH:17]3)[cH:18][cH:19][cH:20][n:21]12 | CC(=O)OCc1cccn2c(C)cnc12.Sc1nc2ccccc2[nH]1 | Cc1cnc2c(CSc3nc4ccccc4[nH]3)cccn12 | null | null | C(C)(=O)O.Br | Heteroatom Alkylation and Arylation | OtherReaction | a6a1a19cf663515a44b0f453ada37e5a4daffb7fa3d960443c6193f945fe684c | c1c742f57df6accfc044260f03f42fd14bb3b3abd9eed9176ff83ab0921ba9e6 | c1ccc2[nH]c(SCc3cccn4ccnc34)nc2c1 | C-C(=O)-O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:9].[SH;D1;+0:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]:1):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:9] | 64.9 | [{"value": 64.9, "product": "CC1=CN=C2N1C=CC=C2CSC2=NC1=C(N2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5.0 g (30 mmole) of 3-(acetoxymethyl)-2-pyridinamine and 4.8 g (35 mmole) of 2-bromopropanal spontaneously heated upon mixing. After cooling, the mixture was partitioned between aqueous potassium carbonate and dichloromethane. The organic phase was separated, washed with water, dried over magnesium sulfate... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic thiol | Monosulfide | null | null | c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | HO- | C(C)(=O)O.Br | null | null | CC(=O)OCc1cccn2c(C)cnc12.Sc1nc2ccccc2[nH]1>C(C)(=O)O.Br>Cc1cnc2c(CSc3nc4ccccc4[nH]3)cccn12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f84ba9f8e5be4beca7f52a1b1da276df | Nc1ncccc1CO.O=C(CBr)c1ccccc1>>OCc1cccn2cc(-c3ccccc3)nc12 | OCC=1C(=NC=CC1)N.BrCC(=O)C1=CC=CC=C1>>OCC=1C=2N(C=CC1)C=C(N2)C2=CC=CC=C2 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:17]1[NH2:16].O=[C:9]([CH2:8]Br)[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:16][c:17]12 | Nc1ncccc1CO.O=C(CBr)c1ccccc1 | OCc1cccn2cc(-c3ccccc3)nc12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:11](:[c:12]:[c:13]):[c:9](:[c:10]):[n;H0;D2;+0:8]:1):[c:6]:[c:7] | 62.4 | [{"value": 62.4, "product": "OCC=1C=2N(C=CC1)C=C(N2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1.24 g (10 mmole) of 3-hydroxymethyl-2-pyridinamine and 2.0 g (10 mmole) of α-bromoacetophenone in 25 ml of ethanol was stirred at room temperature. After 18 hours the resultant solid was collected, washed with ethano, and dissolved in water. The solution was made basic with aqueous potassium carbonate and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | C(C)O | null | null | Nc1ncccc1CO.O=C(CBr)c1ccccc1>C(C)O>OCc1cccn2cc(-c3ccccc3)nc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-836256bfef694ba9a01186c6ce27e48e | OCc1cccn2cc(-c3ccccc3)nc12.Sc1nc2ccccc2[nH]1>>c1ccc(-c2cn3cccc(CSc4nc5ccccc5[nH]4)c3n2)cc1 | C([O-])([O-])=O.[K+].[K+].SC=1NC2=C(N1)C=CC=C2.OCC=1C=2N(C=CC1)C=C(N2)C2=CC=CC=C2.C(C)(=O)O>>C1(=CC=CC=C1)C=1N=C2N(C=CC=C2CSC2=NC3=C(N2)C=CC=C3)C1 | O[CH2:12][c:11]1[cH:10][cH:9][cH:8][n:7]2[cH:6][c:5](-[c:4]3[cH:3][cH:2][cH:1][cH:26][cH:25]3)[n:24][c:23]21.[SH:13][c:14]1[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[nH:22]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][n:7]3[cH:8][cH:9][cH:10][c:11]([CH2:12][S:13][c:14]4[n:15][c:16]5[cH:17][cH:18][cH:19][cH:20][c:21]5... | OCc1cccn2cc(-c3ccccc3)nc12.Sc1nc2ccccc2[nH]1 | c1ccc(-c2cn3cccc(CSc4nc5ccccc5[nH]4)c3n2)cc1 | null | null | O.Br | Heteroatom Alkylation and Arylation | OtherReaction | c119424abb7b621e5fb126e8156c5e4310815e8f2d609f48f2eb427b327d29ac | c1ccf05c97341d9cf75acae4c03f7d5a8212340a35905af6c8d60b4ccc775d1f | c1ccc(-c2cn3cccc(CSc4nc5ccccc5[nH]4)c3n2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:9].[SH;D1;+0:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]:1):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1:[c:9] | null | [] | null | null | null | null | A mixture of 1.24 g (10 mmole) of 3-hydroxymethyl-2-pyridinamine and 2.0 g (10 mmole) of α-bromoacetophenone in 25 ml of ethanol was stirred at room temperature. After 18 hours the resultant solid was collected, washed with ethano, and dissolved in water. The solution was made basic with aqueous potassium carbonate and... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccn2ccnc2c1.c1ccc2[nH]cnc2c1 | HO- | O.Br | null | null | OCc1cccn2cc(-c3ccccc3)nc12.Sc1nc2ccccc2[nH]1>O.Br>c1ccc(-c2cn3cccc(CSc4nc5ccccc5[nH]4)c3n2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ec4b142bf5f74761be211a314d93711e | CC(=O)OCc1cccnc1N.O=CC(Br)c1ccccc1>>CC(=O)OCc1cccn2c(-c3ccccc3)cnc12 | C(C)(=O)OCC=1C(=NC=CC1)N.BrC(C=O)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)OCC=1C=2N(C=CC1)C(=CN2)C2=CC=CC=C2 | [CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10][c:20]1[NH2:19].O=[CH:18][CH:11](Br)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10]2[c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][n:19][c:20]12 | CC(=O)OCc1cccnc1N.O=CC(Br)c1ccccc1 | CC(=O)OCc1cccn2c(-c3ccccc3)cnc12 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 3a7835efa5ac56b87be43234b54606ae621fc957a5ff407573e590f6174c2545 | 4efe5597cd78b75eedda88a299158b349ae1f03c7cd5a6a1daf8cec0515aae7c | c1ccc(-c2cnc3ccccn23)cc1 | Br-[CH;D3;+0:1](-[CH;D2;+0:2]=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[n;H0;D2;+0:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1:[c:12]:[c:13]):[c:6]:[c:7] | 59.2 | [{"value": 59.2, "product": "C(C)(=O)OCC=1C=2N(C=CC1)C(=CN2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4.4 g (26 mmole) of 3-(acetoxymethyl)-2-pyridinamine and 6.0 g (30 mmole) of 2-bromo-2-phenylacetaldehyde was heated at 65°. The mixture was dissolved in water, made basic with aqueous potassium carbonate, and extracted with dichloromethane. The organic layer was washed with water, dried over magnesium sul... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HBr | O | null | null | CC(=O)OCc1cccnc1N.O=CC(Br)c1ccccc1>O>CC(=O)OCc1cccn2c(-c3ccccc3)cnc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a780a0ca91834f50975115462cbc9747 | BrBr.CCOC=Cc1ccc([N+](=O)[O-])cc1>>O=CC(Br)c1ccc([N+](=O)[O-])cc1 | BrC1=CC=C(C=C1)[N+](=O)[O-].C(=C)OCC.C(C)N(CC)CC.C([O-])(O)=O.[Na+].C(C)OC=CC1=CC=C(C=C1)[N+](=O)[O-].BrBr>>BrC(C=O)C1=CC=C(C=C1)[N+](=O)[O-] | Br[Br:4].CC[O:1][CH:2]=[CH:3][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1>>[O:1]=[CH:2][CH:3]([Br:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1 | BrBr.CCOC=Cc1ccc([N+](=O)[O-])cc1 | O=CC(Br)c1ccc([N+](=O)[O-])cc1 | null | C(C)(=O)[O-].[Pb+2].C(C)(=O)[O-].C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C | O.C(C)OCC | Acylation | OtherReaction | f5d66695b2f9e53c76aca010c41d0cb63deb432e034f424288d4848a778add72 | 4e7055dd1a6f8a019617555fc7ce04fcc074194de52588b968b185a843befa5c | c1ccccc1 | Br-[Br;H0;D1;+0:1].C-C-[O;H0;D2;+0:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[Br;H0;D1;+0:1]-[CH;D3;+0:4](-[CH;D2;+0:3]=[O;H0;D1;+0:2])-[c:5](:[c:6]):[c:7] | 106.5 | [{"value": 106.5, "product": "BrC(C=O)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 16.0 g (80 mmole) of 1-bromo-4-nitrobenzene, 11.2 ml (ca. 120 mmole) of ethyl vinyl ether, 179.2 mg of lead(II) acetate, 484 mg of tri-o-tolylphosphine, and 22 ml (ca. 160 mmole) of triethylamine was placed in a bomb, purged with nitrogen, and heated at 100° for eight hours. The reaction mixture was partit... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary halide.Aldehyde | null | null | c1ccccc1 | HBr | C(C)(=O)[O-].[Pb+2].C(C)(=O)[O-].C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.O.C(C)OCC | null | 2 | BrBr.CCOC=Cc1ccc([N+](=O)[O-])cc1>C(C)(=O)[O-].[Pb+2].C(C)(=O)[O-].C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.O.C(C)OCC>O=CC(Br)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a21645fac4664fb38a4001103a9d3541 | Nc1ncccc1CO.O=CC(Br)c1ccc([N+](=O)[O-])cc1>>O=[N+]([O-])c1ccc(-c2cn3cccc(CO)c3n2)cc1 | OCC=1C(=NC=CC1)N.BrC(C=O)C1=CC=C(C=C1)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+]>>OCC=1C=2N(C=CC1)C=C(N2)C2=CC=C(C=C2)[N+](=O)[O-] | [n:10]1[cH:11][cH:12][cH:13][c:14]([CH2:15][OH:16])[c:17]1[NH2:18].O=[CH:9][CH:8](Br)[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:20][cH:19]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][cH:12][cH:13][c:14]([CH2:15][OH:16])[c:17]3[n:18]2)[cH:19][cH:20]1 | Nc1ncccc1CO.O=CC(Br)c1ccc([N+](=O)[O-])cc1 | O=[N+]([O-])c1ccc(-c2cn3cccc(CO)c3n2)cc1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 3a7835efa5ac56b87be43234b54606ae621fc957a5ff407573e590f6174c2545 | 4efe5597cd78b75eedda88a299158b349ae1f03c7cd5a6a1daf8cec0515aae7c | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[CH;D3;+0:1](-[CH;D2;+0:2]=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[c:13]:[c:12]:[n;H0;D3;+0:11]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[n;H0;D2;+0:8]:[c:9]:1:[c:10] | 70.3 | [{"value": 70.3, "product": "OCC=1C=2N(C=CC1)C=C(N2)C2=CC=C(C=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 16.0 g (80 mmole) of 1-bromo-4-nitrobenzene, 11.2 ml (ca. 120 mmole) of ethyl vinyl ether, 179.2 mg of lead(II) acetate, 484 mg of tri-o-tolylphosphine, and 22 ml (ca. 160 mmole) of triethylamine was placed in a bomb, purged with nitrogen, and heated at 100° for eight hours. The reaction mixture was partit... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HBr | ClCCl | null | null | Nc1ncccc1CO.O=CC(Br)c1ccc([N+](=O)[O-])cc1>ClCCl>O=[N+]([O-])c1ccc(-c2cn3cccc(CO)c3n2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-86536fe8661e486a88a22adbeb7d5c2f | Cc1ccc(-c2cnc3c(CSc4nc5ccccc5[nH]4)cccn23)cc1.O>>Cc1ccc(-c2cnc3c(CS(=O)c4nc5ccccc5[nH]4)cccn23)cc1 | O.CC1=CC=C(C=C1)C1=CN=C2N1C=CC=C2CSC2=NC1=C(N2)C=CC=C1.CC1=CC=C(C=C1)C1=CN=C2N1C=CC=C2CSC2=NC1=C(N2)C=CC=C1.N1C=NC2=C1C=CC=C2>>CC1=CC=C(C=C1)C1=CN=C2N1C=CC=C2CS(=O)C2=NC1=C(N2)C=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]3[c:10]([CH2:11][S:12][c:14]4[n:15][c:16]5[cH:17][cH:18][cH:19][cH:20][c:21]5[nH:22]4)[cH:23][cH:24][cH:25][n:26]23)[cH:27][cH:28]1.[OH2:13]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]3[c:10]([CH2:11][S:12](=[O:13])[c:14]4[n:15][c:16]5[cH:17][cH:18][cH:1... | Cc1ccc(-c2cnc3c(CSc4nc5ccccc5[nH]4)cccn23)cc1.O | Cc1ccc(-c2cnc3c(CS(=O)c4nc5ccccc5[nH]4)cccn23)cc1 | null | null | null | Oxidation | Sulfanyl to sulfinyl_H2O | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=S(Cc1cccn2c(-c3ccccc3)cnc12)c1nc2ccccc2[nH]1 | [#7;a:1]:[c:2](:[#7;a:3]):[c:4]-[C:5]-[S;H0;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:1.[OH2;D0;+0:12]>>[#7;a:1]:[c:2](:[#7;a:3]):[c:4]-[C:5]-[S;H0;D3;+0:6](=[O;H0;D1;+0:12])-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | 56 | [{"value": 56.0, "product": "CC1=CC=C(C=C1)C1=CN=C2N1C=CC=C2CS(=O)C2=NC1=C(N2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (801 mg) was prepared by the method of Example 2 using 1.38 g (3.7 mmole) of 2-[[[3-(4-methylphenyl)imidazo[1,2-a]pyridin-8-yl]methyl]thio]-1H-benzimidazole hemihydrate (see Example 53) instead of 2-[(imidazo[1,2-a]pyridin-8-yl]methyl)thio]-1H-benzimidazole. Structure assignment was supported by the ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | null | null | null | null | Cc1ccc(-c2cnc3c(CSc4nc5ccccc5[nH]4)cccn23)cc1.O>>Cc1ccc(-c2cnc3c(CS(=O)c4nc5ccccc5[nH]4)cccn23)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-64220bd736cf4a15b5080fe21f5358c6 | CC(C)(C)C(=O)Cl.Cc1cccc(N)n1>>Cc1cccc(NC(=O)C(C)(C)C)n1 | O.NC1=NC(=CC=C1)C.C(C)N(CC)CC.CC(C(=O)Cl)(C)C>>CC(C(=O)NC1=NC(=CC=C1)C)(C)C | Cl[C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[CH3:13].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[n:14]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[CH3:13])[n:14]1 | CC(C)(C)C(=O)Cl.Cc1cccc(N)n1 | Cc1cccc(NC(=O)C(C)(C)C)n1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11] | 68 | [{"value": 68.0, "product": "CC(C(=O)NC1=NC(=CC=C1)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a cold (ca. 0°) solution of 86.4 g (0.88 mole) of 2-amino-6-methylpyridine and 101 g (0.96 mole) of triethylamine in 1.0 liter of dichloromethane was added dropwise a solution of 106.1 g (0.88 mole) of trimethylacetyl chloride in 100 ml of dichloromethane. After stirring an hour after addition was completed, the mix... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | ClCCl | null | null | CC(C)(C)C(=O)Cl.Cc1cccc(N)n1>ClCCl>Cc1cccc(NC(=O)C(C)(C)C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f7e10d9962e6410cbb9a8290ea6e5a72 | CC(C)(C#N)N=NC(C)(C)C#N.Cc1cccc(NC(=O)C(C)(C)C)n1.O=C1CCC(=O)N1Br.Sc1nc2ccccc2[nH]1>>Nc1cccc(CSc2nc3ccccc3[nH]2)n1.Nc1cccc(CSc2nc3ccccc3[nH]2)n1.O | N(=NC(C#N)(C)C)C(C#N)(C)C.CC(C(=O)NC1=NC(=CC=C1)C)(C)C.C(Cl)(Cl)(Cl)Cl.SC=1NC2=C(N1)C=CC=C2.BrN1C(CCC1=O)=O>>O.N1C(=NC2=C1C=CC=C2)SCC2=CC=CC(=N2)N.N2C(=NC1=C2C=CC=C1)SCC1=CC=CC(=N1)N | C[C:29](C)([C:21]#[N:19])[N:28]=[N:17][C:16]([C:15]#N)([CH3:25])[CH3:30].C[C:13](C)(C(=O)[NH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[n:18]1)[CH3:14].O=[C:20]1[CH2:22][CH2:23][C:24](=[O:37])[N:36]1Br.[SH:8][c:9]1[n:10][c:11]2[cH:12][cH:31][cH:32][cH:33][c:34]2[nH:35]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][S:8][... | CC(C)(C#N)N=NC(C)(C)C#N.Cc1cccc(NC(=O)C(C)(C)C)n1.O=C1CCC(=O)N1Br.Sc1nc2ccccc2[nH]1 | Nc1cccc(CSc2nc3ccccc3[nH]2)n1.Nc1cccc(CSc2nc3ccccc3[nH]2)n1.O | null | null | C(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | 95dc9e8ba5c9220952767cf012fd03d5f189dc3865df8fc52ae52e1e5505e737 | fdd6f6dae7d53d2bdcd6b8b502f1d71a1445b3dc22133d47ee163ea5c123f264 | c1ccc(CSc2nc3ccccc3[nH]2)nc1.c1ccc(CSc2nc3ccccc3[nH]2)nc1 | Br-[N;H0;D3;+0:1]1-[C;H0;D3;+0:2](=O)-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5]-1=[O;H0;D1;+0:6].C-[C;H0;D4;+0:7](-C)(-[C;H0;D2;+0:8]#[N;H0;D1;+0:9])-[N;H0;D2;+0:10]=[N;H0;D2;+0:11]-[C;H0;D4;+0:12](-[CH3;D1;+0:13])(-[CH3;D1;+0:14])-[C;H0;D2;+0:15]#N.C-[C;H0;D4;+0:16](-C)(-[CH3;D1;+0:17])-C(=O)-[NH;D2;+0:18]-[c:19](:[c... | null | [] | null | null | null | null | To a cold (ca. 0°) solution of 86.4 g (0.88 mole) of 2-amino-6-methylpyridine and 101 g (0.96 mole) of triethylamine in 1.0 liter of dichloromethane was added dropwise a solution of 106.1 g (0.88 mole) of trimethylacetyl chloride in 100 ml of dichloromethane. After stirring an hour after addition was completed, the mix... | 10.6084/m9.figshare.5104873.v1 | null | Diazene.Nitrile.Nitrile.Secondary amide.Tertiary amide.Tertiary amide.Aromatic thiol | Primary amine.Primary amine.Monosulfide.Monosulfide | C1CC[NH]C1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccncc1.c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1.c1ccncc1.c1ccc2[nH]cnc2c1 | HBr | C(C)(C)O | null | null | CC(C)(C#N)N=NC(C)(C)C#N.Cc1cccc(NC(=O)C(C)(C)C)n1.O=C1CCC(=O)N1Br.Sc1nc2ccccc2[nH]1>C(C)(C)O>Nc1cccc(CSc2nc3ccccc3[nH]2)n1.Nc1cccc(CSc2nc3ccccc3[nH]2)n1.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9a013dcaa09647d4a94926a17285746e | Nc1cccc(CSc2nc3ccccc3[nH]2)n1>>c1ccc2[nH]c(SCc3cccc4nccn34)nc2c1 | O.N1C(=NC2=C1C=CC=C2)SCC2=CC=CC(=N2)N.N2C(=NC1=C2C=CC=C1)SCC1=CC=CC(=N1)N.ClCC=O.C([O-])(O)=O.[Na+]>>N=1C=CN2C1C=CC=C2CSC2=NC1=C(N2)C=CC=C1 | [cH:1]1[cH:2][cH:3][c:4]2[nH:5][c:6]([S:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[n:17]3)[n:18][c:19]2[cH:20]1>>[cH:1]1[cH:2][cH:3][c:4]2[nH:5][c:6]([S:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][c:13]4[n:14][cH:15][cH:16][n:17]34)[n:18][c:19]2[cH:20]1 | Nc1cccc(CSc2nc3ccccc3[nH]2)n1 | c1ccc2[nH]c(SCc3cccc4nccn34)nc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 6d486165009112780e608dff97176824bff10b35baa5286e796a3ea4a90aee71 | 0c2e6cfe0bdb8f8cd78303a7637b3ef339f807f5bc27c4a22ad516ce20b37476 | c1ccc2[nH]c(SCc3cccc4nccn34)nc2c1 | [C:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5](-[NH2;D1;+0:6]):[c:7]>>[C:1]-[c:2](:[c:3]):[n;H0;D3;+0:4]1:[c:8]:[c:9]:[n;H0;D2;+0:6]:[c:5]:1:[c:7] | 93.7 | [{"value": 93.7, "product": "N=1C=CN2C1C=CC=C2CSC2=NC1=C(N2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a cold (ca. 0°) solution of 86.4 g (0.88 mole) of 2-amino-6-methylpyridine and 101 g (0.96 mole) of triethylamine in 1.0 liter of dichloromethane was added dropwise a solution of 106.1 g (0.88 mole) of trimethylacetyl chloride in 100 ml of dichloromethane. After stirring an hour after addition was completed, the mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccc2[nH]cnc2c1.c1ccn2ccnc2c1 | Other | C(C)O | null | null | Nc1cccc(CSc2nc3ccccc3[nH]2)n1>C(C)O>c1ccc2[nH]c(SCc3cccc4nccn34)nc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6c40390b38bd4fa3b03a4392347326e9 | CCOC(=O)CC(=O)Nc1nccs1.O=c1oc(C(Cl)Cl)nc2c(C(F)(F)F)cccc12>>CCOC(=O)C(C(=O)Nc1nccs1)C(=O)c1cccc(C(F)(F)F)c1NC(=O)C(Cl)Cl | Cl.ClC(C1=NC2=C(C(O1)=O)C=CC=C2C(F)(F)F)Cl.S1C(=NC=C1)NC(CC(=O)OCC)=O.[OH-].[Na+]>>ClC(C(=O)NC1=C(C=CC=C1C(F)(F)F)C(C(C(=O)OCC)C(=O)NC=1SC=CN1)=O)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[NH:9][c:10]1[n:11][cH:12][cH:13][s:14]1.[c:15]1(=[O:16])[c:17]2[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[c:26]2[n:27][c:28]([CH:30]([Cl:31])[Cl:32])[o:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[NH:9][c:10]1[n:11][cH:12][cH:13][s:14]1)[... | CCOC(=O)CC(=O)Nc1nccs1.O=c1oc(C(Cl)Cl)nc2c(C(F)(F)F)cccc12 | CCOC(=O)C(C(=O)Nc1nccs1)C(=O)c1cccc(C(F)(F)F)c1NC(=O)C(Cl)Cl | null | null | O1CCCC1.O | C-C Coupling | OtherReaction | 8856744ee3cb90f6b6957ff9f302c5dbf4db43e678d7b3f2b4a6f42fa45ab704 | 5d7d6595fe09ebcc762e41ef3c2e96a31baab898c63543fdc1edff7a49f34b57 | O=C(CC(=O)c1ccccc1)Nc1nccs1 | [#16;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]):[#7;a:11].[Cl;D1;H0:12]-[C:13](-[Cl;D1;H0:14])-[c;H0;D3;+0:15]1:[n;H0;D2;+0:16]:[c:17](:[c:18]):[c:19](:[c:20]):[c;H0;D3;+0:21](=[O;D1;H0:22]):[o;H0;D2;+0:23]:1>>[#16;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6](-[C:7](=... | 98.9 | [{"value": 98.9, "product": "ClC(C(=O)NC1=C(C=CC=C1C(F)(F)F)C(C(C(=O)OCC)C(=O)NC=1SC=CN1)=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 30 | MINUTE | At 20° C., 150 g of 2-dichloromethyl-8-trifluoromethyl-4H-3,1-benzoxazine-4-one, 120 g of ethyl 3-(2-thiazolylamino)-3-oxo-propanoate and 1.5 liters of tetrahydrofuran were mixed together and stirred for 30 minutes and then, while maintaining the temperature at 20° C., 40 g of sodium hydroxide in flakes were added ther... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone.Ester.Secondary amide | c1nc2ccccc2co1 | c1ccccc1 | c1cscn1.c1ccccc1 | null | O1CCCC1.O | 20 | 0.5 | CCOC(=O)CC(=O)Nc1nccs1.O=c1oc(C(Cl)Cl)nc2c(C(F)(F)F)cccc12>O1CCCC1.O>CCOC(=O)C(C(=O)Nc1nccs1)C(=O)c1cccc(C(F)(F)F)c1NC(=O)C(Cl)Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-12b979f700884044918f9eed66626663 | CC(C)C(Cl)c1nc2c(C(F)(F)F)cccc2c(=O)o1.CCOC(=O)CC(=O)Nc1nccs1>>CCOC(=O)C(C(=O)Nc1nccs1)C(=O)c1cccc(C(F)(F)F)c1NC(=O)C(Cl)C(C)C | Cl.ClC(C(C)C)C1=NC2=C(C(O1)=O)C=CC=C2C(F)(F)F.S1C(=NC=C1)NC(CC(=O)OCC)=O.[H-].[Na+]>>ClC(C(=O)NC1=C(C=CC=C1C(F)(F)F)C(C(C(=O)OCC)C(=O)NC=1SC=CN1)=O)C(C)C | [c:15]1(=[O:16])[c:17]2[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[c:26]2[n:27][c:28]([CH:30]([Cl:31])[CH:32]([CH3:33])[CH3:34])[o:29]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[NH:9][c:10]1[n:11][cH:12][cH:13][s:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[NH:9][c:10]1[n:11][cH:1... | CC(C)C(Cl)c1nc2c(C(F)(F)F)cccc2c(=O)o1.CCOC(=O)CC(=O)Nc1nccs1 | CCOC(=O)C(C(=O)Nc1nccs1)C(=O)c1cccc(C(F)(F)F)c1NC(=O)C(Cl)C(C)C | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 8856744ee3cb90f6b6957ff9f302c5dbf4db43e678d7b3f2b4a6f42fa45ab704 | 5d7d6595fe09ebcc762e41ef3c2e96a31baab898c63543fdc1edff7a49f34b57 | O=C(CC(=O)c1ccccc1)Nc1nccs1 | [#16;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]):[#7;a:11].[C:12]-[C:13](-[Cl;D1;H0:14])-[c;H0;D3;+0:15]1:[n;H0;D2;+0:16]:[c:17](:[c:18]):[c:19](:[c:20]):[c;H0;D3;+0:21](=[O;D1;H0:22]):[o;H0;D2;+0:23]:1>>[#16;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6](-[C:7](=[O;D1;H... | 72.2 | [{"value": 72.2, "product": "ClC(C(=O)NC1=C(C=CC=C1C(F)(F)F)C(C(C(=O)OCC)C(=O)NC=1SC=CN1)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Under an inert gas, 5.52 g of sodium hydride dispersed at 55% in oil and 173 ml of tetrahydrofuran were mixed together and then a solution of 26.22 g of ethyl 3-(2-thiazolylamino)-3-oxo-propanoate in 690 ml of tetrahydrofuran was added slowly at 20° C. After stirring for 10 minutes, a solution of 34.5 g of 2-(1-chloro-... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone.Ester.Secondary amide | c1nc2ccccc2co1 | c1ccccc1 | c1cscn1.c1ccccc1 | null | O1CCCC1 | null | 0.166667 | CC(C)C(Cl)c1nc2c(C(F)(F)F)cccc2c(=O)o1.CCOC(=O)CC(=O)Nc1nccs1>O1CCCC1>CCOC(=O)C(C(=O)Nc1nccs1)C(=O)c1cccc(C(F)(F)F)c1NC(=O)C(Cl)C(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8157287710cc4674bb21ea720e6e9ab7 | CC(C)(C)C(Cl)c1nc2c(C(F)(F)F)cccc2c(=O)o1.CCOC(=O)CC(=O)Nc1nccs1>>CCOC(=O)C(C(=O)Nc1nccs1)C(=O)c1cccc(C(F)(F)F)c1NC(=O)C(Cl)C(C)(C)C | S1C(=NC=C1)NC(CC(=O)OCC)=O.ClC(C(C)(C)C)C1=NC2=C(C(O1)=O)C=CC=C2C(F)(F)F>>ClC(C(=O)NC1=C(C=CC=C1C(F)(F)F)C(C(C(=O)OCC)C(=O)NC=1SC=CN1)=O)C(C)(C)C | [c:15]1(=[O:16])[c:17]2[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[c:26]2[n:27][c:28]([CH:30]([Cl:31])[C:32]([CH3:33])([CH3:34])[CH3:35])[o:29]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[NH:9][c:10]1[n:11][cH:12][cH:13][s:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[NH:9][c:10]1[n... | CC(C)(C)C(Cl)c1nc2c(C(F)(F)F)cccc2c(=O)o1.CCOC(=O)CC(=O)Nc1nccs1 | CCOC(=O)C(C(=O)Nc1nccs1)C(=O)c1cccc(C(F)(F)F)c1NC(=O)C(Cl)C(C)(C)C | null | null | null | C-C Coupling | OtherReaction | 8856744ee3cb90f6b6957ff9f302c5dbf4db43e678d7b3f2b4a6f42fa45ab704 | 5d7d6595fe09ebcc762e41ef3c2e96a31baab898c63543fdc1edff7a49f34b57 | O=C(CC(=O)c1ccccc1)Nc1nccs1 | [#16;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]):[#7;a:11].[C:12]-[C:13](-[Cl;D1;H0:14])-[c;H0;D3;+0:15]1:[n;H0;D2;+0:16]:[c:17](:[c:18]):[c:19](:[c:20]):[c;H0;D3;+0:21](=[O;D1;H0:22]):[o;H0;D2;+0:23]:1>>[#16;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6](-[C:7](=[O;D1;H... | 88.5 | [{"value": 88.5, "product": "ClC(C(=O)NC1=C(C=CC=C1C(F)(F)F)C(C(C(=O)OCC)C(=O)NC=1SC=CN1)=O)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Step A of Example 4, 7.7 g of ethyl 3-(2-thiazolylamino)-3-oxo-propanoate and 10.55 g of 2-(1-chloro-2,2-dimethylpropyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-one [prepared according to the process described in the European Pat. No. 0040573] were reacted to obtain 15.6 g of ethyl 2-[(2-chloro-1-... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone.Ester.Secondary amide | c1nc2ccccc2co1 | c1ccccc1 | c1cscn1.c1ccccc1 | null | null | null | null | CC(C)(C)C(Cl)c1nc2c(C(F)(F)F)cccc2c(=O)o1.CCOC(=O)CC(=O)Nc1nccs1>>CCOC(=O)C(C(=O)Nc1nccs1)C(=O)c1cccc(C(F)(F)F)c1NC(=O)C(Cl)C(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-49dc0c00fc3c4e21999c01b2300b26ae | CCOC(=O)c1ccc(C)nc1.CCOC(C)=O>>CCOC(=O)CC(=O)c1ccc(C)nc1 | Cl.C(C)OC(C1=CN=C(C=C1)C)=O.C(C)(=O)OCC.C(C)OC(C1=CN=C(C=C1)C)=O.C[O-].[Na+]>>C(C)OC(CC(C1=CN=C(C=C1)C)=O)=O | CCO[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]1 | CCOC(=O)c1ccc(C)nc1.CCOC(C)=O | CCOC(=O)CC(=O)c1ccc(C)nc1 | null | null | O.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 66fad61539a4377b2099bf2b4bbabe7e2e80878fd5eeb84b925f14180416e99f | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[#8:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:12])-[CH2;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 33.6 | [{"value": 33.6, "product": "C(C)OC(CC(C1=CN=C(C=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | 35.8 g (0.52 mol) of sodium methylate and 200 ml of toluene were put in a 750-ml sulfonation flask. The reaction mixture was heated to reflux temperature. A mixture of 55.7 g (0.33 mol) of 6-methyl nicotinic acid ethyl ester (produced according to Swiss Patent No. 654 577) and 60.3 g (0.68 mol) of ethyl acetate was add... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | null | c1ccncc1 | HO- | O.C1(=CC=CC=C1)C | 20 | null | CCOC(=O)c1ccc(C)nc1.CCOC(C)=O>O.C1(=CC=CC=C1)C>CCOC(=O)CC(=O)c1ccc(C)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4a9ec14af0274134a654dea42067722b | CCOC(=O)CC(=O)c1ccc(C)nc1>>CCOC(=O)CC(O)c1ccc(C)nc1 | C(C)OC(CC(C1=CN=C(C=C1)C)=O)=O.[H][H]>>C(C)OC(CC(C=1C=CC(=NC1)C)O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([OH:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]1 | CCOC(=O)CC(=O)c1ccc(C)nc1 | CCOC(=O)CC(O)c1ccc(C)nc1 | null | [Pd] | C(C)O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccncc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12] | null | [] | null | null | 6 | HOUR | 10.0 g (0.048 mol) of 6-methyl nicotinoyl acetic acid ethyl ester (distilled) was dissolved in 200 ml of 95 percent ethanol, mixed with 1 g of 5 percent palladium on activated carbon and poured into a 1-liter autoclave. The autoclave was put under 10 bars of hydrogen and stirred at 20°. The hydrogenation ended after 6 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccncc1 | null | [Pd].C(C)O | null | 6 | CCOC(=O)CC(=O)c1ccc(C)nc1>[Pd].C(C)O>CCOC(=O)CC(O)c1ccc(C)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-eb4ae90a1b0b41d0abcdfe869a7b004c | CC(=O)OC(C)=O.CCOC(=O)CC(O)c1ccc(C)nc1>>CCOC(=O)CC(OC(C)=O)c1ccc(C)nc1 | C(C)OC(CC(C=1C=CC(=NC1)C)O)=O.C(C)(=O)OC(C)=O>>C(C)OC(CC(C=1C=CC(=NC1)C)OC(C)=O)=O | CC(=O)O[C:9]([CH3:10])=[O:11].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([OH:8])[c:12]1[cH:13][cH:14][c:15]([CH3:16])[n:17][cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([O:8][C:9]([CH3:10])=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH3:16])[n:17][cH:18]1 | CC(=O)OC(C)=O.CCOC(=O)CC(O)c1ccc(C)nc1 | CCOC(=O)CC(OC(C)=O)c1ccc(C)nc1 | null | CN(C1=CC=NC=C1)C | C(C)(=O)OCC | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | c1ccncc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]:[c:6]-[C:7](-[OH;D1;+0:8])-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12]>>[#7;a:4]:[c:5]:[c:6]-[C:7](-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12])-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 100.9 | [{"value": 100.9, "product": "C(C)OC(CC(C=1C=CC(=NC1)C)OC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 6 | HOUR | 45.9 g (0.22 mol) of 3-hydroxy-3-(2-methyl-5-pyridyl)-propionic acid ethyl ester was dissolved in 100 ml of ethyl acetate, and 50 ml (0.53 mol) of acetic anhydride and 0.1 g (0.82 mmol) of 4-dimethylaminopyridine were added. The solution was stirred for 6 hours at 20° C. and then evaporated. The residue was dissolved i... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | c1ccncc1 | HO- | CN(C1=CC=NC=C1)C.C(C)(=O)OCC | 20 | 6 | CC(=O)OC(C)=O.CCOC(=O)CC(O)c1ccc(C)nc1>CN(C1=CC=NC=C1)C.C(C)(=O)OCC>CCOC(=O)CC(OC(C)=O)c1ccc(C)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6fcb5bbb70f740b3b196d7724ee508c4 | COC(=O)CC(O)c1ccc(C)nc1>>COC(=O)CCc1ccc(C)nc1 | CO.C(C)(=O)OC(C)=O.COC(CC(C=1C=CC(=NC1)C)O)=O.[H][H]>>COC(CCC=1C=CC(=NC1)C)=O | O[CH:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:7]1[cH:8][cH:9][c:10]([CH3:11])[n:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH3:11])[n:12][cH:13]1 | COC(=O)CC(O)c1ccc(C)nc1 | COC(=O)CCc1ccc(C)nc1 | null | [Pd] | C(C)(=O)O.C1(=CC=CC=C1)C | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccncc1 | O-[CH;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11] | 114 | [{"value": 114.0, "product": "COC(CCC=1C=CC(=NC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | 80.0 g (0.35 mol) of recrystallized 3-hydroxy-3-(2-methyl-5-pyridyl)-propionic acid methyl ester was dissolved in 100 ml of toluene. 60.0 g (0.588 mol) of acetic anhydride and 0.1 g (0.0009 mol) of 4-dimethyl-aminopyridine were added, and the solution was stirred for 1 hour at 60° C. Then 20 ml of methanol was added. A... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccncc1 | Other | [Pd].C(C)(=O)O.C1(=CC=CC=C1)C | 60 | 1 | COC(=O)CC(O)c1ccc(C)nc1>[Pd].C(C)(=O)O.C1(=CC=CC=C1)C>COC(=O)CCc1ccc(C)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0b3d34b04fcc487eb0025ec6b261350a | O=C1OC(=O)[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1>>O=C1OC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | [BH4-].[Li+].C(C1=CC=CC=C1)N1C(N([C@H]2[C@@H]1C(OC2=O)=O)CC2=CC=CC=C2)=O.C(C)N(CC)CC.S1C=C(C=C1)C([C@H](C)O)C1=CSC=C1.Cl>>C(C1=CC=CC=C1)N1C(N([C@H]2[C@@H]1COC2=O)CC2=CC=CC=C2)=O | O=[C:4]1[O:3][C:2](=[O:1])[C@@H:6]2[C@H:5]1[N:17]([CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[C:15](=[O:16])[N:7]2[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]1[O:3][CH2:4][C@H:5]2[C@@H:6]1[N:7]([CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15](=[O:16])[N:17]2[CH2:18][c:19]1[cH:20][cH:2... | O=C1OC(=O)[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | O=C1OC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | null | null | O1CCCC1 | Reduction | OtherReaction | e60d179fa838932638136b9288d8f7af33b66a192c06e8a70acbb0229c36e424 | 4b654437278f0c5453f0be55bc4b7cc1e4b1f390efee313efdd366ce1b3701ec | O=C1OC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | O=[C;H0;D3;+0:1]1-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]2-[#7:6]-[C:7](=[O;D1;H0:8])-[#7:9](-[C:10])-[C:11]-2-1>>[C:10]-[#7:9]1-[C:7](=[O;D1;H0:8])-[#7:6]-[C:5]2-[C:3](=[O;D1;H0:4])-[#8:2]-[CH2;D2;+0:1]-[C:11]-1-2 | null | [] | null | null | 1.5 | HOUR | 0.336 g (1 mmol) of cis-1,3-dibenzyl-hexahydro-1H-furo[3,4-d]imidazole-2,4,6-trione in 3.3 ml of tetrahydrofuran are placed in an apparatus standing under argon. There is then added dropwise within 15 minutes at room temperature a solution of 0.15 ml (1.1 mmol) of triethylamine and 0.224 g (1 mmol) of [S]-1,1-di-(3-thi... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ester | C1[NH][C@H]2COC[C@H]2[NH]1 | C1[NH][C@H]2COC[C@H]2[NH]1 | c1ccccc1.C1[NH][C@H]2COC[C@H]2[NH]1.c1ccccc1 | Other | O1CCCC1 | null | 1.5 | O=C1OC(=O)[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1>O1CCCC1>O=C1OC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a443e942722a4e3ba0857f61fd906fce | O=C1OC(=O)[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1>>O=C1OC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | Cl.[BH4-].[Li+].C(C1=CC=CC=C1)N1C(N([C@H]2[C@@H]1C(OC2=O)=O)CC2=CC=CC=C2)=O.C1(=CC=CC=C1)C(C(C)O)(C)C1=CC=CC=C1.C(C)N(CC)CC.[H-]>>C(C1=CC=CC=C1)N1C(N([C@H]2[C@@H]1COC2=O)CC2=CC=CC=C2)=O | O=[C:4]1[O:3][C:2](=[O:1])[C@@H:6]2[C@H:5]1[N:17]([CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[C:15](=[O:16])[N:7]2[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]1[O:3][CH2:4][C@H:5]2[C@@H:6]1[N:7]([CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15](=[O:16])[N:17]2[CH2:18][c:19]1[cH:20][cH:2... | O=C1OC(=O)[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | O=C1OC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Reduction | OtherReaction | e60d179fa838932638136b9288d8f7af33b66a192c06e8a70acbb0229c36e424 | 4b654437278f0c5453f0be55bc4b7cc1e4b1f390efee313efdd366ce1b3701ec | O=C1OC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | O=[C;H0;D3;+0:1]1-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]2-[#7:6]-[C:7](=[O;D1;H0:8])-[#7:9](-[C:10])-[C:11]-2-1>>[C:10]-[#7:9]1-[C:7](=[O;D1;H0:8])-[#7:6]-[C:5]2-[C:3](=[O;D1;H0:4])-[#8:2]-[CH2;D2;+0:1]-[C:11]-1-2 | 51.7 | [{"value": 51.7, "product": "C(C1=CC=CC=C1)N1C(N([C@H]2[C@@H]1COC2=O)CC2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 30 | MINUTE | 0.673 g (2 mmol) of cis-1,3-dibenzyl-hexahydro-1H-furo[3,4-d]imidazole-2,4,6-trione and 0.435 g (2 mmol) of (-)-3,3-diphenyl-2-butanol ([α]36520 =-338.9° (1% in ethanol)) in 5 ml of toluene are heated under reflux for 6 hours in an apparatus standing under argon. After cooling 0.28 ml (2 mmol) of triethylamine and 5 ml... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ester | C1[NH][C@H]2COC[C@H]2[NH]1 | C1[NH][C@H]2COC[C@H]2[NH]1 | c1ccccc1.C1[NH][C@H]2COC[C@H]2[NH]1.c1ccccc1 | Other | O1CCCC1.C1(=CC=CC=C1)C | 60 | 0.5 | O=C1OC(=O)[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1>O1CCCC1.C1(=CC=CC=C1)C>O=C1OC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-230c462de1a74c1688f3fcda4928a955 | C[N+](=O)[O-].O=Cc1cccc(Cl)c1Cl>>O=[N+]([O-])C=Cc1cccc(Cl)c1Cl | ClC1=C(C=O)C=CC=C1Cl.C(C)(=O)[O-].[NH4+].[N+](=O)([O-])C.C(C)(=O)O>>ClC1=C(C=CC=C1Cl)C=C[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[CH3:4].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13]>>[O:1]=[N+:2]([O-:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13] | C[N+](=O)[O-].O=Cc1cccc(Cl)c1Cl | O=[N+]([O-])C=Cc1cccc(Cl)c1Cl | null | null | C(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#7;+:6](-[O;-;D1;H0:7])=[O;D1;H0:8]>>[O;-;D1;H0:7]-[#7;+:6](=[O;D1;H0:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | 28.0 g of 2,3-dichlorobenzaldehyde, 13.9 g of ammonium acetate, 13.9 ml of nitromethane and 120 ml of glacial acetic acid are refluxed for 2 hours. After cooling, the reaction mixture is poured onto ice and stirred for 30 minutes. The formed precipitate is then filtered off, washed with water and dried in vacuo to thus... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | 0.5 | C[N+](=O)[O-].O=Cc1cccc(Cl)c1Cl>C(Cl)(Cl)Cl>O=[N+]([O-])C=Cc1cccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-558e3460c7e744ffa8db86530f4fe9eb | N#CC=CN1CCOCC1.O=[N+]([O-])C=Cc1cccc(Cl)c1Cl>>N#CC(=CN1CCOCC1)C(C[N+](=O)[O-])c1cccc(Cl)c1Cl | ClC1=C(C=CC=C1Cl)C=C[N+](=O)[O-].O1CCN(CC1)C=CC#N.O1CCCC1>>O1CCN(CC1)C=C(C(C[N+](=O)[O-])C1=C(C(=CC=C1)Cl)Cl)C#N | [N:1]#[C:2][CH:3]=[CH:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.[CH:11](=[CH:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[c:22]1[Cl:23]>>[N:1]#[C:2][C:3](=[CH:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[CH:11]([CH2:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[c:22]... | N#CC=CN1CCOCC1.O=[N+]([O-])C=Cc1cccc(Cl)c1Cl | N#CC(=CN1CCOCC1)C(C[N+](=O)[O-])c1cccc(Cl)c1Cl | null | null | C(Cl)(Cl)Cl | C-C Coupling | OtherReaction | a8dc4f9b59203ac9839a7af10c3b32dfeb02a432fd7e8c9a8c486b1aa91291e3 | 7c70f6c231ffa6706c78b969e714efbaf69be23bd6f1e9785c5fc574ed76d8c9 | C(=CN1CCOCC1)Cc1ccccc1 | [#7:1]-[C:2]=[CH;D2;+0:3]-[C:4]#[N;D1;H0:5].[O;-;D1;H0:6]-[#7;+:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#7:1]-[C:2]=[C;H0;D3;+0:3](-[C:4]#[N;D1;H0:5])-[CH;D3;+0:10](-[CH2;D2;+0:9]-[#7;+:7](-[O;-;D1;H0:6])=[O;D1;H0:8])-[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | 5.0 g of 1-(2',3'-dichlorophenyl)-2-nitroethylene, 3.18 g of 3-morpholinoacrylonitrile and 30 ml of tetrahydrofuran (abs.) are refluxed for 24 hours, and the reaction solution is subsequently concentrated by evaporation. The resulting residue, dissolved in toluene/ethyl acetate (2:1 V/V), is chromatographed through sil... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine | Enamine.Nitro group | null | null | C1COCC[NH]1.c1ccccc1 | null | C(Cl)(Cl)Cl | null | null | N#CC=CN1CCOCC1.O=[N+]([O-])C=Cc1cccc(Cl)c1Cl>C(Cl)(Cl)Cl>N#CC(=CN1CCOCC1)C(C[N+](=O)[O-])c1cccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-33bb59becf104684a1b21b5c19697b00 | C=CCN1CCOCC1.CCC=O>>CC=CN1CCOCC1 | C(C=C)N1CCOCC1.N1CCOCC1.C([O-])([O-])=O.[K+].[K+].C(CC)=O>>O1CCN(CC1)C=CC | C=CC[N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1.O=[CH:3][CH2:2][CH3:1]>>[CH3:1][CH:2]=[CH:3][N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1 | C=CCN1CCOCC1.CCC=O | CC=CN1CCOCC1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 51c2e5f5abcd10a95c6bf8004436abbc32ce5a9826fca8fa4483db82244f49da | 5f124e679fe439a249e688220225601edc9f8f57cb8f36db744fb3714c9bb2f8 | C1COCCN1 | C=C-C-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O=[CH;D2;+0:7]-[CH2;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:9]-[CH;D2;+0:8]=[CH;D2;+0:7]-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1 | null | [] | -5 | CELSIUS | 2 | HOUR | A 500 ml 4-neck flask was equipped with a stirrer, thermometer, addition funnel and condenser. To the flask was charged 191.7 g (2.2 m) of morpholine and 138.2 g (1 m) of potassium carbonate (anhydrous) and the mixture was stirred and cooled to -5° C. with an ice-salt bath. To the flask was added 58 g (1 m) of propiona... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Tertiary amine.Allyl | Enamine | C1COCC[NH]1 | C1COCC[NH]1 | C1COCC[NH]1 | HO- | CS(=O)C | -5 | 2 | C=CCN1CCOCC1.CCC=O>CS(=O)C>CC=CN1CCOCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-629bbd2014a249eeba8a9b2d984002ca | O=C(O)[C@@H]1CCCN1C(=O)OCc1ccccc1.O=C1CCC(=O)N1O>>O=C(ON1C(=O)CCC1=O)[C@@H]1CCCN1C(=O)OCc1ccccc1 | N1([C@H](C(=O)O)CCC1)C(=O)OCC1=CC=CC=C1.ON1C(CCC1=O)=O.C1(CCCCC1)N=C=NC1CCCCC1>>N1([C@H](C(=O)ON2C(=O)CCC2=O)CCC1)C(=O)OCC1=CC=CC=C1 | O[C:2](=[O:1])[C@@H:11]1[CH2:12][CH2:13][CH2:14][N:15]1[C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[OH:3][N:4]1[C:5](=[O:6])[CH2:7][CH2:8][C:9]1=[O:10]>>[O:1]=[C:2]([O:3][N:4]1[C:5](=[O:6])[CH2:7][CH2:8][C:9]1=[O:10])[C@@H:11]1[CH2:12][CH2:13][CH2:14][N:15]1[C:16](=[O:17])[O:18][CH2:19][c:2... | O=C(O)[C@@H]1CCCN1C(=O)OCc1ccccc1.O=C1CCC(=O)N1O | O=C(ON1C(=O)CCC1=O)[C@@H]1CCCN1C(=O)OCc1ccccc1 | null | null | O1CCOCC1 | Protection | OtherReaction | a1b3ee4184fc00a0730e4c14eca3a5fbe87fccb44744074c13ef1bfbfabde8ad | e66168e1cfeb6611d93ee4c49193aae81e56c700a9fe46743dc42eed291ed0f9 | O=C(ON1C(=O)CCC1=O)[C@@H]1CCCN1C(=O)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9].[O;D1;H0:10]=[C:11]1-[C:12]-[C:13]-[C:14](=[O;D1;H0:15])-[#7:16]-1-[OH;D1;+0:17]>>[#8:7]-[C:6](=[O;D1;H0:8])-[#7:5](-[C:9])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:17]-[#7:16]1-[C:14](=[O;D1;H0:15])-[C:13]-[C:12]-[C:11]-1=[O;... | null | [] | null | null | 8 | HOUR | Z-Pro (7.5 gm, 0.03 mole) and N-Hydroxysuccinimide (3.45 gm, 0.03 mole) were dissolved in cold dioxane and dicyclohexylcarbodiimide (DCC) (6.18 gm, 0.03 mole) was added with rapid stirring. The mixture was stirred overnight at room temperature and the next day the solid dicyclohexylurea (DCU) was filtered off. The solv... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | C1CC[NH]C1.C1CC[NH]C1.c1ccccc1 | HO- | O1CCOCC1 | null | 8 | O=C(O)[C@@H]1CCCN1C(=O)OCc1ccccc1.O=C1CCC(=O)N1O>O1CCOCC1>O=C(ON1C(=O)CCC1=O)[C@@H]1CCCN1C(=O)OCc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-be399e7199704e30bda4410c3cde43ec | CCC1CCCCC1O>>CCC1CCCCC1=O | CCOCC.C(C)C1C(CCCC1)O.CC(=O)C.C(C)(C)O>>C(C)C1C(CCCC1)=O | [CH3:1][CH2:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[OH:9]>>[CH3:1][CH2:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1=[O:9] | CCC1CCCCC1O | CCC1CCCCC1=O | null | null | CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 53141f2efd300d3d12cff5c9fb9e873d72703f640e8dc954cbc8bc774c6bb175 | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCCCC1 | [C:1]-[C:2](-[C:3])-[CH;D3;+0:4](-[OH;D1;+0:5])-[C:6]-[C:7]>>[C:1]-[C:2](-[C:3])-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6]-[C:7] | 91.3 | [{"value": 91.0, "product": "C(C)C1C(CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "C(C)C1C(CCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Ethylcyclohexanol (1.6 moles, 204 g, 226 mL) was stirred in 3.21 of acetone at 0° C. and treated with 8N Jones reagent (prepared from 106.8 g of CrO3 suspended in 92 mL of concentrated sulfuric acid and diluted to 400 mL with water) until the orange color persisted (~430 mL). Isopropanol was then added to turn the so... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | null | CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O | null | null | CCC1CCCCC1O>CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>CCC1CCCCC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d7dda766e6354321bedff8272e2cb95b | CCC1(CC(=O)OC)CCCCC1=O>>CCC1(CC(=O)OC)CCC=CC1=O | O.COC(CC1(C(CCCC1)=O)CC)=O.OO.C1(=CC=CC=C1)[Se]Cl>>COC(CC1(C(C=CCC1)=O)CC)=O | [CH3:1][CH2:2][C:3]1([CH2:4][C:5](=[O:6])[O:7][CH3:8])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[O:14]>>[CH3:1][CH2:2][C:3]1([CH2:4][C:5](=[O:6])[O:7][CH3:8])[CH2:9][CH2:10][CH:11]=[CH:12][C:13]1=[O:14] | CCC1(CC(=O)OC)CCCCC1=O | CCC1(CC(=O)OC)CCC=CC1=O | null | null | O1CCCC1.C(C)(=O)OCC | Oxidation | OtherReaction | c3f46dece7d561c52f40f0751c15f974be9b38efb558b193b8501b4052d952a3 | 67a464903031b8397675aaf6feadeebae3d7c0396776afb6b950bc78e0b26b98 | O=C1C=CCCC1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1>>[O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-1 | 55.3 | [{"value": 55.0, "product": "COC(CC1(C(C=CCC1)=O)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.3, "product": "COC(CC1(C(C=CCC1)=O)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | The ketone, 2-carbomethoxymethyl-2-ethylcyclohexanone (IX) (141 mmol, 28 g) was stirred in 1.25 l of ethyl acetate (dried over 3A molecular sieves) and treated with 169 mmol (32.5 g) of PhSeCl. The reaction was stirred under nitrogen for 4 hours then treated with 250 mL of water. The mixture was shaken vigorously in a ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1CCCCC1 | C1=CCCCC1 | C1=CCCCC1 | null | O1CCCC1.C(C)(=O)OCC | null | 4 | CCC1(CC(=O)OC)CCCCC1=O>O1CCCC1.C(C)(=O)OCC>CCC1(CC(=O)OC)CCC=CC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1ce98538753c4615be5ca5b3ffca31d6 | Nc1cccc(F)c1F>>NNc1cccc(F)c1F | NC(=O)N.N(=O)[O-].[Na+].FC1=C(N)C=CC=C1F>>FC1=C(C=CC=C1F)NN | [NH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1[F:10]>>[NH2:1][NH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1[F:10] | Nc1cccc(F)c1F | NNc1cccc(F)c1F | null | null | Cl.O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 98.5 | [{"value": 49.0, "product": "FC1=C(C=CC=C1F)NN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "FC1=C(C=CC=C1F)NN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | In each of two flasks, 775 mmol (100 g) of 2,3-difluoroaniline were added to 2 L of concentrated hydrochloric acid at -15° C. and treated dropwise with a solution of 852 mmol (58.9 g) of sodium nitrite in 500 mL of water. Ten minutes after the addition, the reaction was treated with 930 mmol (55.8 g) of urea. This was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | Cl.O | null | 0.333333 | Nc1cccc(F)c1F>Cl.O>NNc1cccc(F)c1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-03e4bd88d1ce42acb287f7b9043ba591 | CCCc1cc(=O)n(C)[nH]1.O=C(Cl)c1ccccc1Cl>>CCCc1nn(C)c(O)c1C(=O)c1ccccc1Cl | Cl.CN1NC(=CC1=O)CCC.[OH-].[Ca+2].[OH-].ClC1=C(C(=O)Cl)C=CC=C1>>CN1N=C(C(=C1O)C(C1=C(C=CC=C1)Cl)=O)CCC | [CH3:1][CH2:2][CH2:3][c:4]1[nH:5][n:6]([CH3:7])[c:8](=[O:9])[cH:10]1.Cl[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][n:6]([CH3:7])[c:8]([OH:9])[c:10]1[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19] | CCCc1cc(=O)n(C)[nH]1.O=C(Cl)c1ccccc1Cl | CCCc1nn(C)c(O)c1C(=O)c1ccccc1Cl | null | null | O1CCOCC1.C1=CC=CC=C1 | C-C Coupling | OtherReaction | 07614a477505845b8b00881e95dcf5a4ae1c1e6ccda2ebbb502b43e7fe69c96b | e1b08acf756cad98d86825b025be6920975410ce1fb4391267cab0f06479c4dd | O=C(c1ccccc1)c1cn[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[c:7]1:[cH;D2;+0:8]:[c;H0;D3;+0:9](=[O;H0;D1;+0:10]):[#7;a:11](-[C;D1;H3:12]):[nH;D2;+0:13]:1>>[C:6]-[c:7]1:[n;H0;D2;+0:13]:[#7;a:11](-[C;D1;H3:12]):[c;H0;D3;+0:9](-[OH;D1;+0:10]):[c;H0;D3;+0:8]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 9.2 | [{"value": 9.2, "product": "CN1N=C(C(=C1O)C(C1=C(C=CC=C1)Cl)=O)CCC", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | 1.4 g. of 1-methyl-3-n-propyl-5-pyrazolone is dissolved in 10 ml. of dioxane with heating and then 1.5 g. of calcium hydroxide is added to the resulting solution. 1.75 g. of 2-chlorobenzoyl chloride is added dropwise with stirring at 50° C. After completion of the dropwise addition, the mixture is heated under reflux f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone.Aromatic alcohol | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HCl | O1CCOCC1.C1=CC=CC=C1 | 50 | null | CCCc1cc(=O)n(C)[nH]1.O=C(Cl)c1ccccc1Cl>O1CCOCC1.C1=CC=CC=C1>CCCc1nn(C)c(O)c1C(=O)c1ccccc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4b1389322ed646e284965de33facdb73 | Cc1nn(C)c(Cl)c1C(=O)c1ccc(Cl)cc1Cl.S>>Cc1nn(C)c(S)c1C(=O)c1ccc(Cl)cc1Cl | ClC1=C(C(=NN1C)C)C(C1=C(C=C(C=C1)Cl)Cl)=O.S.[Na]>>CN1N=C(C(=C1S)C(C1=C(C=C(C=C1)Cl)Cl)=O)C | Cl[c:6]1[n:4]([CH3:5])[n:3][c:2]([CH3:1])[c:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]1[Cl:18].[SH2:7]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([SH:7])[c:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]1[Cl:18] | Cc1nn(C)c(Cl)c1C(=O)c1ccc(Cl)cc1Cl.S | Cc1nn(C)c(S)c1C(=O)c1ccc(Cl)cc1Cl | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1dcc849acbb941aabde5621ae3b910771d16b68e8c484971351400893b9a31f3 | 5acfc94bcb91f90cc14ddd9f791d64cf2f45381ebe181eac63cc3d2843bb00cd | O=C(c1ccccc1)c1cn[nH]c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2](-[C;D1;H3:3]):[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[C:8](=[O;D1;H0:9])-[c:10].[SH2;D0;+0:11]>>[C;D1;H3:6]-[c:5]1:[#7;a:4]:[#7;a:2](-[C;D1;H3:3]):[c;H0;D3;+0:1](-[SH;D1;+0:11]):[c:7]:1-[C:8](=[O;D1;H0:9])-[c:10] | 33.3 | [{"value": 33.3, "product": "CN1N=C(C(=C1S)C(C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.3 g. of 5-chloro-4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazole, 2.1 g. of sodium hydrogen sulfide 2 hydrate and 6 ml. of ethanol is heated under reflux on a water bath for 3 hours. After completion of the reaction, the ethanol is distilled off under reduced pressure from the reaction mixture and 15 ml. of... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic thiol | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HCl | C(C)O | null | null | Cc1nn(C)c(Cl)c1C(=O)c1ccc(Cl)cc1Cl.S>C(C)O>Cc1nn(C)c(S)c1C(=O)c1ccc(Cl)cc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-476cce7d76254fa8842f62307dfdb1cf | Cc1nn(C)c(Cl)c1C(=O)c1c(Cl)cccc1Cl.[OH-]>>Cc1nn(C)c(O)c1C(=O)c1c(Cl)cccc1Cl | O.[OH-].[K+].ClC1=C(C(=NN1C)C)C(C1=C(C=CC=C1Cl)Cl)=O>>CN1N=C(C(=C1O)C(C1=C(C=CC=C1Cl)Cl)=O)C | Cl[c:6]1[n:4]([CH3:5])[n:3][c:2]([CH3:1])[c:8]1[C:9](=[O:10])[c:11]1[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18].[OH-:7]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([OH:7])[c:8]1[C:9](=[O:10])[c:11]1[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18] | Cc1nn(C)c(Cl)c1C(=O)c1c(Cl)cccc1Cl.[OH-] | Cc1nn(C)c(O)c1C(=O)c1c(Cl)cccc1Cl | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b4258126c167496f538cf970a39e4dd99d63172899e93a0d1e07cc27e688cc5f | 05ba928edd770174a8e0738270a5c99182284743586e41e52e6183b77c44ac41 | O=C(c1ccccc1)c1cn[nH]c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2](-[C;D1;H3:3]):[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[C:8](=[O;D1;H0:9])-[c:10].[OH-;D0:11]>>[C;D1;H3:6]-[c:5]1:[#7;a:4]:[#7;a:2](-[C;D1;H3:3]):[c;H0;D3;+0:1](-[OH;D1;+0:11]):[c:7]:1-[C:8](=[O;D1;H0:9])-[c:10] | 48 | [{"value": 48.0, "product": "CN1N=C(C(=C1O)C(C1=C(C=CC=C1Cl)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In 5 ml. of water is dissolved 0.56 g. of potassium hydroxide and a solution of 1.52 g. of 5-chloro-4-(2,6-dichlorobenzoyl)-1,3-dimethylpyrazole in 10 ml. of ethanol is added thereto. The mixture is heated under reflux for 12 hours. After completion of the reaction, the reaction mixture is allowed to cool and extracted... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic alcohol | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | Other | C(C)O | null | null | Cc1nn(C)c(Cl)c1C(=O)c1c(Cl)cccc1Cl.[OH-]>C(C)O>Cc1nn(C)c(O)c1C(=O)c1c(Cl)cccc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bc3a3565d5d142ffbb06c41f2d0202a5 | CC(=O)Cl.Cc1nn(C)c(O)c1C(=O)c1ccccc1Cl>>CC(=O)Oc1c(C(=O)c2ccccc2Cl)c(C)nn1C | C(C)(=O)Cl.C1=CC=CC=C1.C(C)N(CC)CC.CN1N=C(C(=C1O)C(C1=C(C=CC=C1)Cl)=O)C>>CN1N=C(C(=C1OC(C)=O)C(C1=C(C=CC=C1)Cl)=O)C | Cl[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[Cl:15])[c:16]([CH3:17])[n:18][n:19]1[CH3:20]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[Cl:15])[c:16]([CH3:17])[n:18][n:19]1[CH3:20] | CC(=O)Cl.Cc1nn(C)c(O)c1C(=O)c1ccccc1Cl | CC(=O)Oc1c(C(=O)c2ccccc2Cl)c(C)nn1C | null | null | O | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C(c1ccccc1)c1cn[nH]c1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C;D1;H3:4]-[#7;a:5]1:[#7;a:6]:[c:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:11]:1-[OH;D1;+0:12]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:12]-[c:11]1:[#7;a:5](-[C;D1;H3:4]):[#7;a:6]:[c:7]:[c:8]:1-[C:9]=[O;D1;H0:10] | 82.2 | [{"value": 82.2, "product": "CN1N=C(C(=C1OC(C)=O)C(C1=C(C=CC=C1)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a mixture of 20 ml. of benzene and 0.51 g. of triethylamine is dissolved 1.25 g. of 1,3-dimethyl-4-(2-chlorobenzoyl)-5-hydroxypyrazole and 0.4 g. of acetyl chloride is added dropwise at room temperature with stirring. After completion of the dripwise addition, the mixture is stirred at room temperature for 3 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1cn[nH]c1.c1ccccc1 | HCl | O | null | null | CC(=O)Cl.Cc1nn(C)c(O)c1C(=O)c1ccccc1Cl>O>CC(=O)Oc1c(C(=O)c2ccccc2Cl)c(C)nn1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-29168e56b38d477a98530fbcc396bc0d | Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl.O=C(Cl)CCl>>Cc1nn(C)c(OC(=O)CCl)c1C(=O)c1ccc(Cl)cc1Cl | ClCC(=O)Cl.C1=CC=CC=C1.C(C)N(CC)CC.C1=CC=CC=C1.CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C>>CN1N=C(C(=C1OC(CCl)=O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C | [CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([OH:7])[c:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]1[Cl:22].Cl[C:8](=[O:9])[CH2:10][Cl:11]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([O:7][C:8](=[O:9])[CH2:10][Cl:11])[c:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]1[Cl:22] | Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl.O=C(Cl)CCl | Cc1nn(C)c(OC(=O)CCl)c1C(=O)c1ccc(Cl)cc1Cl | null | null | CCOCC | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C(c1ccccc1)c1cn[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[C;D1;H3:5]-[#7;a:6]1:[#7;a:7]:[c:8]:[c:9](-[C:10]=[O;D1;H0:11]):[c:12]:1-[OH;D1;+0:13]>>[C;D1;H3:5]-[#7;a:6]1:[#7;a:7]:[c:8]:[c:9](-[C:10]=[O;D1;H0:11]):[c:12]:1-[O;H0;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4] | 82 | [{"value": 82.0, "product": "CN1N=C(C(=C1OC(CCl)=O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a mixture of 10 ml. of benzene and 0.2 ml. of triethylamine is dissolved 0.285 g. of 1,3-dimethyl-4-(2.4-dichlorobenzoyl)-5-hydroxypyrazole and then a solution of 0.18 g. of chloroacetylchloride in 5 ml. of benzene is added dropwise under ice-cooling and stirring. After completion of the dropwise addition, the resul... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1cn[nH]c1.c1ccccc1 | HCl | CCOCC | null | null | Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl.O=C(Cl)CCl>CCOCC>Cc1nn(C)c(OC(=O)CCl)c1C(=O)c1ccc(Cl)cc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-178c86032d3a41a895b268140b3e00cd | COC(=O)Cl.Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl>>COC(=O)Oc1c(C(=O)c2ccc(Cl)cc2Cl)c(C)nn1C | C(OC)(=O)Cl.C1=CC=CC=C1.C(C)N(CC)CC.CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C>>CN1N=C(C(=C1OC(=O)OC)C(C1=C(C=C(C=C1)Cl)Cl)=O)C | Cl[C:3]([O:2][CH3:1])=[O:4].[OH:5][c:6]1[c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[Cl:17])[c:18]([CH3:19])[n:20][n:21]1[CH3:22]>>[CH3:1][O:2][C:3](=[O:4])[O:5][c:6]1[c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[Cl:17])[c:18]([CH3:19])[n:20][n:21]1[CH3:22] | COC(=O)Cl.Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl | COC(=O)Oc1c(C(=O)c2ccc(Cl)cc2Cl)c(C)nn1C | null | null | O | Acylation | Schotten-Baumann to ester | 18e63da6830cc445f43af5e9dc21618a6276c35c0e735b25c948aaaf35c35656 | 9d4bf8407389b23766af8e91d21ef1aae6a051b3a051fef2f77a7ae83951845d | O=C(c1ccccc1)c1cn[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C;D1;H3:5]-[#7;a:6]1:[#7;a:7]:[c:8]:[c:9](-[C:10]=[O;D1;H0:11]):[c:12]:1-[OH;D1;+0:13]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:13]-[c:12]1:[#7;a:6](-[C;D1;H3:5]):[#7;a:7]:[c:8]:[c:9]:1-[C:10]=[O;D1;H0:11] | 92 | [{"value": 92.0, "product": "CN1N=C(C(=C1OC(=O)OC)C(C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | In a mixture of 20 ml. of dry benzene and 0.28 g. of triethylamine is dissolved 0.72 g. of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole and then 0.26 g. of methyl chlorocarbonate is added dropwise at room temperature with stirring. After completion of the dropwise addition, the mixture is stirred at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1cn[nH]c1.c1ccccc1 | HCl | O | null | 12 | COC(=O)Cl.Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl>O>COC(=O)Oc1c(C(=O)c2ccc(Cl)cc2Cl)c(C)nn1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b66e7becec724b6491382205cc770ac9 | [Ca+2]>>[Ca] | [Cl-].[Ca+2].[Cl-].CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C.[OH-].[Na+]>>[Ca].CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C | [Ca+2:19]>>[Ca:19] | [Ca+2] | [Ca] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [Ca+2;H0;D0:1]>>[Ca;H0;D0;+0:1] | 79 | [{"value": 79.0, "product": "[Ca].CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In 50 ml. of water is suspended 2.85 g. of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole and the suspension is dissolved in about 5 ml. of a 2N aqueous solution of sodium hydroxide. A solution of 1.11 g. of calcium chloride in 10 ml. of water is added and the resulting mixture is stirred. The so separated prec... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | [Ca+2]>O>[Ca] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-76d147b435c04a7b955366b32a5b6d8a | Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl>>Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl | CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C.C(C)(C)N>>C(C)(C)N.CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C | [CH3:5][c:6]1[n:7][n:8]([CH3:9])[c:10]([OH:11])[c:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]1[Cl:22]>>[CH3:5][c:6]1[n:7][n:8]([CH3:9])[c:10]([OH:11])[c:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]1[Cl:22] | Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl | Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl | null | null | C1=CC=CC=C1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(c1ccccc1)c1cn[nH]c1 | null | 93.2 | [{"value": 93.2, "product": "C(C)(C)N.CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In 50 ml. of benzene is suspended 2.85 g. of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole and 0.7 g. of isopropylamine is added to the suspension with stirring. Then, the resulting mixture is stirred at room temperature for about 1 hour. The solvent is distilled off from the reaction mixture. The residue is c... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1cn[nH]c1.c1ccccc1 | null | C1=CC=CC=C1 | null | null | Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl>C1=CC=CC=C1>Cc1nn(C)c(O)c1C(=O)c1ccc(Cl)cc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d4dd3618695e44f1baef211e20a3427b | Cl>>Cl | CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C.Cl>>Cl.CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C | [ClH:19]>>[ClH:19] | Cl | Cl | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 57.1 | [{"value": 57.1, "product": "Cl.CN1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To 0.3 g of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole is added 2 ml. of conc. HCl and the resulting mixture is stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture is allowed to cool and the so separated desired product is recovered by filtration. The product is w... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | Cl>>Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5c5da0b5b6994d0ba89697fc67f6989a | C=CCN1N=C(C)CC1=O.O=C(Cl)c1ccc(Cl)cc1Cl>>C=CCn1nc(C)c(C(=O)c2ccc(Cl)cc2Cl)c1O | C(C=C)N1N=C(CC1=O)C.[OH-].[Ca+2].[OH-].ClC1=C(C(=O)Cl)C=CC(=C1)Cl>>C(C=C)N1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C | [CH2:1]=[CH:2][CH2:3][N:4]1[N:5]=[C:6]([CH3:7])[CH2:8][C:19]1=[O:20].Cl[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]1[Cl:18]>>[CH2:1]=[CH:2][CH2:3][n:4]1[n:5][c:6]([CH3:7])[c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])[c:19]1[OH:20] | C=CCN1N=C(C)CC1=O.O=C(Cl)c1ccc(Cl)cc1Cl | C=CCn1nc(C)c(C(=O)c2ccc(Cl)cc2Cl)c1O | null | null | C(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | aac6dc6526ae8c2f685594db2ccc9b10ca38fb900446d895b359b141c461fa53 | 2f56b7230f74fb4d0cafa1ae54b83b0f3bb2b8005b63c194a6d47c0427dd5799 | O=C(c1ccccc1)c1cn[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H2:6]=[C:7]-[C:8]-[N;H0;D3;+0:9]1-[N;H0;D2;+0:10]=[C;H0;D3;+0:11](-[C;D1;H3:12])-[CH2;D2;+0:13]-[C;H0;D3;+0:14]-1=[O;H0;D1;+0:15]>>[C;D1;H2:6]=[C:7]-[C:8]-[n;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[C;D1;H3:12]):[c;H0;D3;+0:13](-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 40.7 | [{"value": 40.7, "product": "C(C=C)N1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A suspension of 1.4 g. of 1-allyl-3-methyl-2-pyrazolin-5-one and 0.74 g. of calcium hydroxide in 20 ml. of isopropanol is heated under reflux with stirring for 1.5 hours. After cooling, to the resulting mixture is added dropwise 2.3 g. of 2,4-dichlorobenzoyl chloride. After completion of the dropwise addition, the resu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazone amide | Ketone.Aromatic alcohol | C1=N[NH]CC1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HCl | C(C)(C)O | null | 1.5 | C=CCN1N=C(C)CC1=O.O=C(Cl)c1ccc(Cl)cc1Cl>C(C)(C)O>C=CCn1nc(C)c(C(=O)c2ccc(Cl)cc2Cl)c1O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cb26f3ff64eb4b58bd172a8e0c15461a | C=CCn1nc(C)c(C(=O)c2ccc(Cl)cc2Cl)c1O.Cc1ccc(S(=O)(=O)Cl)cc1>>C=CCn1nc(C)c(C(=O)c2ccc(Cl)cc2Cl)c1OS(=O)(=O)c1ccc(C)cc1 | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C=C)N1N=C(C(=C1O)C(C1=C(C=C(C=C1)Cl)Cl)=O)C.C1=CC=CC=C1.C(C)N(CC)CC>>C1(=CC=C(C=C1)S(=O)(=O)OC1=C(C(=NN1CC=C)C)C(C1=C(C=C(C=C1)Cl)Cl)=O)C | [CH2:1]=[CH:2][CH2:3][n:4]1[n:5][c:6]([CH3:7])[c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])[c:19]1[OH:20].Cl[S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][c:27]([CH3:28])[cH:29][cH:30]1>>[CH2:1]=[CH:2][CH2:3][n:4]1[n:5][c:6]([CH3:7])[c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15]... | C=CCn1nc(C)c(C(=O)c2ccc(Cl)cc2Cl)c1O.Cc1ccc(S(=O)(=O)Cl)cc1 | C=CCn1nc(C)c(C(=O)c2ccc(Cl)cc2Cl)c1OS(=O)(=O)c1ccc(C)cc1 | null | null | O | Acylation | Formation of Sulfonic Esters | c2c4b555a0239250a0d50f2987601e44dc9ad17ccca30d564f09f03db5d527db | ac415f683ffa96255e05db6ccff0da77358d24cf1947623a074590b72d5679f2 | O=C(c1ccccc1)c1cn[nH]c1OS(=O)(=O)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H2:7]=[C:8]-[C:9]-[#7;a:10]1:[#7;a:11]:[c:12]:[c:13](-[C:14]=[O;D1;H0:15]):[c:16]:1-[OH;D1;+0:17]>>[C;D1;H2:7]=[C:8]-[C:9]-[#7;a:10]1:[#7;a:11]:[c:12]:[c:13](-[C:14]=[O;D1;H0:15]):[c:16]:1-[O;H0;D2;+0:17]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-... | null | [] | null | null | null | null | To a solution of 180 mg. of 1-allyl-3-methyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole in 6 ml. of benzene and 58.4 mg. of triethylamine is added dropwise 110 mg. of 4-toluenesulfonyl chloride with stirring at room temperature. Then, the resulting mixture is heated under reflux for 1 hours. After completion of the reac... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol.Sulfonyl halide | Tosylate | null | null | c1cn[nH]c1.c1ccccc1.c1ccccc1 | HCl | O | null | null | C=CCn1nc(C)c(C(=O)c2ccc(Cl)cc2Cl)c1O.Cc1ccc(S(=O)(=O)Cl)cc1>O>C=CCn1nc(C)c(C(=O)c2ccc(Cl)cc2Cl)c1OS(=O)(=O)c1ccc(C)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f96a9c2323c64a91af9d9e9bda3f3185 | C1=COCCC1.CC1(C)C(=O)CCC[C@@H]1O>>CC1(C)C(=O)CCC[C@@H]1OC1CCCCO1 | CC1(C(CCC[C@@H]1O)=O)C.O1CCCC=C1.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC1(C(CCC[C@@H]1OC1OCCCC1)=O)C | [CH:11]1=[CH:12][CH2:13][CH2:14][CH2:15][O:16]1.[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[CH2:6][CH2:7][CH2:8][C@@H:9]1[OH:10]>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[CH2:6][CH2:7][CH2:8][C@@H:9]1[O:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:16]1 | C1=COCCC1.CC1(C)C(=O)CCC[C@@H]1O | CC1(C)C(=O)CCC[C@@H]1OC1CCCCO1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | oxa-Michael addition | 7dbeed209463058f59d43728a589e5f7e9550a2179664f08902eb30ad7ba383b | 2683964549e7d2a3e8c7989efc3c7275468eaa2a5d254179937977d9931444d1 | O=C1CCC[C@H](OC2CCCCO2)C1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]-[C:11]=[O;D1;H0:12]>>[C:7]-[C:8](-[O;H0;D2;+0:9]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1)-[C:10]-[C:11]=[O;D1;H0:12] | 99.9 | [{"value": 99.9, "product": "CC1(C(CCC[C@@H]1OC1OCCCC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (3S)-2,2-dimethyl-3-hydroxycyclohexanone (3) (5.12 g, 36.0 mmoles) and dihydropyran (5.00 g., 59.0 mmoles) were dissolved in dry methylene dichloride (90 ml). The solution was cooled in an ice bath, and p-toluenesulfonic acid (50 mg) was added. The resulting mixture was stirred at room temperature for 2 hours. After th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1CCCCC1.C1CCOCC1 | null | C(Cl)Cl | null | 2 | C1=COCCC1.CC1(C)C(=O)CCC[C@@H]1O>C(Cl)Cl>CC1(C)C(=O)CCC[C@@H]1OC1CCCCO1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e006e7b3410346ea9dd39b3dc26dde0d | CCCCSC=C1CC[C@H](OC2CCCCO2)C(C)(C)C1O.CCO.c1ccccc1>>CC1(C)C=C(C=O)CC[C@@H]1OC1CCCCO1.CCCCSC=C1CC[C@H](OC2CCCCO2)C(C)(C)C1=O | C1=CC=CC=C1.C(CCC)SC=C1CC[C@@H](C(C1O)(C)C)OC1OCCCC1.C(C)O>>CC1(C=C(CC[C@@H]1OC1OCCCC1)C=O)C.C(CCC)SC=C1CC[C@@H](C(C1=O)(C)C)OC1OCCCC1 | [CH3:18][CH2:19][CH2:20][CH2:21][S:22][CH:23]=[C:24]1[CH2:25][CH2:26][C@H:27]([O:28][CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33][O:34]2)[C:35]([CH3:36])([CH3:37])[CH:38]1[OH:39].[CH2:6]([OH:7])[CH3:9].[cH:1]1[cH:2][cH:10][cH:3][cH:14][cH:15]1>>[CH3:1][C:2]1([CH3:3])[CH:4]=[C:5]([CH:6]=[O:7])[CH2:8][CH2:9][C@@H:10]1[O:11][C... | CCCCSC=C1CC[C@H](OC2CCCCO2)C(C)(C)C1O.CCO.c1ccccc1 | CC1(C)C=C(C=O)CC[C@@H]1OC1CCCCO1.CCCCSC=C1CC[C@H](OC2CCCCO2)C(C)(C)C1=O | null | C([O-])([O-])=O.[Cd+2].[Hg](Cl)Cl | O | Acylation | OtherReaction | f93b63c106af7fb743dadaa266ae88272007853a5b2f30e1db4a1b356488a86b | 11e2f2a3a54e3ee79261a6771907f730d4589004599a511982bcd13a0c6a2491 | C1=CC[C@@H](OC2CCCCO2)CC1.[CH]=C1CC[C@H](OC2CCCCO2)CC1=O | [#16:1]-[C:2]=[C:3](-[C:4])-[CH;D3;+0:5](-[OH;D1;+0:6])-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10].[CH3;D1;+0:11]-[CH2;D2;+0:12]-[OH;D1;+0:13].[cH;D2;+0:14]1:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:1>>[#16:1]-[C:2]=[C:3](-[C:4])-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9... | null | [] | null | null | 5 | MINUTE | The crude compound (7) (2.00 g), cadmium carbonate (1.10 g, 6.4 mmoles) and mercury dichloride (1.74 g, 6.4 mmoles) were added to 95% ethanol (45 ml), and the solution was stirred for 5 minutes under reflux. After cooling, benzene and water were added, and the mixture was filtered through Celite. The filtrate was extra... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary alcohol | Aldehyde.Ketone.Ether.Ether | C1CCCCC1.c1ccccc1 | C1=CCCCC1.C1CCOCC1.C1CCCCC1 | C1=CCCCC1.C1CCOCC1.C1CCCCC1.C1CCOCC1 | Other | C([O-])([O-])=O.[Cd+2].[Hg](Cl)Cl.O | null | 0.083333 | CCCCSC=C1CC[C@H](OC2CCCCO2)C(C)(C)C1O.CCO.c1ccccc1>C([O-])([O-])=O.[Cd+2].[Hg](Cl)Cl.O>CC1(C)C=C(C=O)CC[C@@H]1OC1CCCCO1.CCCCSC=C1CC[C@H](OC2CCCCO2)C(C)(C)C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-421d6ba424f34877813e82a68e1fedb0 | CC1(C)C=C(C=O)CC[C@@H]1OC1CCCCO1>>CC1(C)C=C(CO)CC[C@@H]1OC1CCCCO1 | CC1(C=C(CC[C@@H]1OC1OCCCC1)C=O)C.C(C)O.[BH4-].[Na+]>>CC1(C=C(CC[C@@H]1OC1OCCCC1)CO)C | [CH3:1][C:2]1([CH3:3])[CH:4]=[C:5]([CH:6]=[O:7])[CH2:8][CH2:9][C@@H:10]1[O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:17]1>>[CH3:1][C:2]1([CH3:3])[CH:4]=[C:5]([CH2:6][OH:7])[CH2:8][CH2:9][C@@H:10]1[O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:17]1 | CC1(C)C=C(C=O)CC[C@@H]1OC1CCCCO1 | CC1(C)C=C(CO)CC[C@@H]1OC1CCCCO1 | null | null | O1CCCC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | C1=CC[C@@H](OC2CCCCO2)CC1 | [C:1]-[C:2]=[C:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5])-[C:6]>>[C:1]-[C:2]=[C:3](-[CH2;D2;+0:4]-[OH;D1;+0:5])-[C:6] | 91.3 | [{"value": 91.3, "product": "CC1(C=C(CC[C@@H]1OC1OCCCC1)CO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.8, "product": "CC1(C=C(CC[C@@H]1OC1OCCCC1)CO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (4S)-3,3-dimethyl-4-tetrahydropyranyloxycyclohexene-1-carbaldehyde (8) (0.71 g, 2.98 mmoles) was dissolved in tetrahydrofuran (7 ml), and a 95% ethanol solution of sodium borohydride (0.38 g, 10 mmoles) was added dropwise over an ice bath. After the addition, the mixture was stirred for 2 hours at a temperature below 1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | C1=CCCCC1.C1CCOCC1 | null | O1CCCC1 | null | 2 | CC1(C)C=C(C=O)CC[C@@H]1OC1CCCCO1>O1CCCC1>CC1(C)C=C(CO)CC[C@@H]1OC1CCCCO1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-43d5bbdfb3f54ea3b1458d64c905aca6 | CC1(C)C=C(CO)CC[C@@H]1OC1CCCCO1.CCOC(C)([O-])[O-]>>C=C1CC[C@H](OC2CCCCO2)C(C)(C)C1CC(=O)OCC | CC1(C=C(CC[C@@H]1OC1OCCCC1)CO)C.C(CC)(=O)O.C(C)(OCC)([O-])[O-]>>C(C)OC(CC1C([C@H](CCC1=C)OC1OCCCC1)(C)C)=O | O[CH2:1][C:2]1=[CH:16][C:13]([CH3:14])([CH3:15])[C@@H:5]([O:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[CH2:4][CH2:3]1.[O-][C:18]([CH3:17])([O-:19])[O:20][CH2:21][CH3:22]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]([O:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[C:13]([CH3:14])([CH3:15])[CH:16]1[CH2:17][C:18](=[O:19])[... | CC1(C)C=C(CO)CC[C@@H]1OC1CCCCO1.CCOC(C)([O-])[O-] | C=C1CC[C@H](OC2CCCCO2)C(C)(C)C1CC(=O)OCC | null | null | null | Acylation | OtherReaction | 0aeeb32c5a75a5f9b69114b449b08187ec3f51e284659fcf65ebe8c78eb55d51 | 8d216031a776a2040811358fc3f0ecf37aeccfba5b9db7c64ebd89f1c71fdb55 | C=C1CCC(OC2CCCCO2)CC1 | O-[CH2;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C:7]-[C:8]-[C:9]-1.[C:10]-[#8:11]-[C;H0;D4;+0:12](-[CH3;D1;+0:13])(-[O-;H0;D1:14])-[O-]>>[C:10]-[#8:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:14])-[CH2;D2;+0:13]-[CH;D3;+0:3]1-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:9]-[C:8]-[C:7]-[C:4]-1(-[C;D1;H3:5])-[C... | 96 | [{"value": 96.0, "product": "C(C)OC(CC1C([C@H](CCC1=C)OC1OCCCC1)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 6 | HOUR | Compound (9) (9.45 g, 39.3 mmoles) and propionic acid were dissolved in newly distilled ethyl ortho-acetate (51.0 g, 314 mmoles). The solution was stirred at 140° C. for 6 hours while distilling off ethanol. Ethyl ortho-acetate was removed from the resulting reaction mixture, and the residue was concentrated. After coo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ester.Vinyl | C1=CCCCC1 | C1CCCCC1 | C1CCCCC1.C1CCOCC1 | HO- | null | 140 | 6 | CC1(C)C=C(CO)CC[C@@H]1OC1CCCCO1.CCOC(C)([O-])[O-]>>C=C1CC[C@H](OC2CCCCO2)C(C)(C)C1CC(=O)OCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2f90b6dd5c40496aa3109111541eaee4 | CC1(C)C=CC[C@]2(C)OC(=O)C[C@H]12>>CC1(C)CCC[C@]2(C)OC(=O)C[C@H]12 | O=C1O[C@@]2([C@H](C1)C(C=CC2)(C)C)C>>O=C1O[C@@]2([C@H](C1)C(CCC2)(C)C)C | [CH3:1][C:2]1([CH3:3])[CH:4]=[CH:5][CH2:6][C@:7]2([CH3:8])[O:9][C:10](=[O:11])[CH2:12][C@H:13]12>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][C@:7]2([CH3:8])[O:9][C:10](=[O:11])[CH2:12][C@H:13]12 | CC1(C)C=CC[C@]2(C)OC(=O)C[C@H]12 | CC1(C)CCC[C@]2(C)OC(=O)C[C@H]12 | null | [Pt]=O | C(C)(=O)O | Reduction | Hydrogenation (double to single) | c54171302ec93808dd1372c8b86c787e430da5c3a7b4fb9f68f64d25f9ebdd1e | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C1C[C@@H]2CCCCC2O1 | [#8:1]-[C:2]1-[C:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[C:9]-1>>[#8:1]-[C:2]1-[C:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[C:9]-1 | 90 | [{"value": 80.0, "product": "O=C1O[C@@]2([C@H](C1)C(CCC2)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": "O=C1O[C@@]2([C@H](C1)C(CCC2)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 23 | HOUR | Compound (13) (1.00 g, 5.55 mmoles) was dissolved in dry acetic acid, and platinum oxide (0.10 g) was added to the solution. The mixture was shaken for 23 hours under hydrogen pressure (30 atms.). The catalyst was separated by filtration, and the filtrate was concentrated under vacuum. The residue was diluted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC[C@@H]2OCC[C@@H]2C1 | C1CC[C@@H]2OCC[C@@H]2C1 | C1CC[C@@H]2OCC[C@@H]2C1 | null | [Pt]=O.C(C)(=O)O | null | 23 | CC1(C)C=CC[C@]2(C)OC(=O)C[C@H]12>[Pt]=O.C(C)(=O)O>CC1(C)CCC[C@]2(C)OC(=O)C[C@H]12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-21bfcba438b74ab0b1de89c3a269dc18 | [Cl][Pt-2]([Cl])([Cl])([Cl])([Cl])[Cl]>>[Pt] | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl.C(=O)=O.C=CC(CCC=C(C)C)=C>>[Pt].C=CC(CCC=C(C)C)=C | [Cl][Pt-2:11]([Cl])([Cl])([Cl])([Cl])[Cl]>>[Pt:11] | [Cl][Pt-2]([Cl])([Cl])([Cl])([Cl])[Cl] | [Pt] | null | null | C(C)(C)O.C(=O)(O)[O-].[Na+] | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | [Cl]-[Pt-2;H0;D6:1](-[Cl])(-[Cl])(-[Cl])(-[Cl])-[Cl]>>[Pt;H0;D0;+0:1] | null | [] | null | null | null | null | The chloroplatinic acid was first dissolved in the isopropanol, NaHCO3 was then added in small portions to avoid the formation of foam, since carbon dioxide was evolved, and the β-myrcene was then added.
Conditions: See reaction.notes.procedure_details.
Workup: was then added in small portions | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | C(C)(C)O.C(=O)(O)[O-].[Na+] | null | null | [Cl][Pt-2]([Cl])([Cl])([Cl])([Cl])[Cl]>C(C)(C)O.C(=O)(O)[O-].[Na+]>[Pt] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c57a0c1cee394dc3b25d45365e2a55ac | CNc1ccccc1.O=[N+]([O-])c1ccccc1>>C=Nc1ccccc1.O=[N+]([O-])c1ccccc1 | NC1=CC=CC=C1.CNC1=CC=CC=C1.[N+](=O)([O-])C1=CC=CC=C1>>[N+](=O)([O-])C1=CC=CC=C1.NC1=CC=CC=C1.C=NC1=CC=CC=C1 | [CH3:1][NH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[O:16]=[N+:17]([O-:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH2:1]=[N:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[O:16]=[N+:17]([O-:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1 | CNc1ccccc1.O=[N+]([O-])c1ccccc1 | C=Nc1ccccc1.O=[N+]([O-])c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 6989a6163e8c6bbd55a2db715ec2211317ff0e491861eac1a12efbbf518e64b5 | 949c4079d4cfdc9fe16404f504e221120066c0603ac761a9f7931fdd0e4dbc8b | c1ccccc1.c1ccccc1 | [CH3;D1;+0:1]-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH2;D1;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | The procedure was the same as for Example 1 with the exception that aniline was omitted from the initial reaction solution. As the reactor contents heated to 160° C., approximately 30% of the nitrobenzene was converted. Complete nitrobenzene conversion required 5.5 hours at 160° C. and yielded 0.068 mole methyl N-pheny... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | null | null | null | c1ccccc1.c1ccccc1 | null | null | 160 | null | CNc1ccccc1.O=[N+]([O-])c1ccccc1>>C=Nc1ccccc1.O=[N+]([O-])c1ccccc1 |
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