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-02ee2261663048188cf6d85d2cc96e3f | ord-c7add3cb537741d8851d853240637af1 | NCCCCN1CCN(c2ncccn2)CC1.O=C1OC(=O)C2CCC1CC2>>O=C1C2CCC(CC2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | C12C(OC(C(CC1)CC2)=O)=O.NCCCCN1CCN(CC1)C1=NC=CC=N1.C12C(OC(C(CC1)CC2)=O)=O.C12C(OC(C(CC1)CC2)=O)=O>>N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)CC2)=O | [NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([c:20]2[n:21][cH:22][cH:23][cH:24][n:25]2)[CH2:26][CH2:27]1.O1[C:2](=[O:1])[CH:3]2[CH2:4][CH2:5][CH:6]([CH2:7][CH2:8]2)[C:9]1=[O:10]>>[O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][CH:6]([CH2:7][CH2:8]2)[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1... | NCCCCN1CCN(c2ncccn2)CC1.O=C1OC(=O)C2CCC1CC2 | O=C1C2CCC(CC2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | null | null | null | Acylation | OtherReaction | e838e371c39fef68334202eb57fea45cf860b0e35038111cff67920eba3c01c8 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C2CCC(CC2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]2-[C:9]-[C:10]-[C:11]-1-[C:12]-[C:13]-2>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]2-[C:9]-[C:10]-[C:11](-[C:12]-[C:13]-2)-[C;H0;D3;+0:5]-1=[O;D1;H0:4] | 8.7 | [{"value": 6.0, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.7, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | An intimate mixture of 0.5 g (2.14 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine and 0.22 g (1.42 mmol) of 3-oxabicyclo[3.2.2]nonan-2,4-dione was heated in an oil bath at 220°-230° C. for 15 minutes. An additional 0.22 g (1.42 mmol) of 3-oxabicyclo[3.2.2]nonan-2,4-dione was added. Heating in an oil bath at 220... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CC2CCC1COC2 | C1CC2CCC1C[NH]C2 | C1C[NH]CC[NH]1.c1cncnc1.C1CC2CCC1C[NH]C2 | HO- | null | null | 0.25 | NCCCCN1CCN(c2ncccn2)CC1.O=C1OC(=O)C2CCC1CC2>>O=C1C2CCC(CC2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9551d7b99ad4419ca95993482a6ed9e7 | O=C(O)[C@@H]1CC[C@H](C(=O)O)CC1>>O=C1OC(=O)C2CCC1CC2 | [C@H]1(CC[C@@H](CC1)C(=O)O)C(=O)O>>C12C(OC(C(CC1)CC2)=O)=O | O[C:4](=[O:5])[C@@H:6]1[CH2:7][CH2:8][C@H:9]([C:2](=[O:1])[OH:3])[CH2:10][CH2:11]1>>[O:1]=[C:2]1[O:3][C:4](=[O:5])[CH:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2 | O=C(O)[C@@H]1CC[C@H](C(=O)O)CC1 | O=C1OC(=O)C2CCC1CC2 | null | null | C(C)(=O)OC(C)=O | Miscellaneous | OtherReaction | 183ae75e2d9e2329faacdc1d2285d85f6c8832b70b979f6eec23dfeb34e2d3f3 | 22fb50577915472f1babb105381e408122dc09b3472eabb73e6e4daecfef90f6 | O=C1OC(=O)C2CCC1CC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@H;D3;+0:3]1-[C:4]-[C:5]-[C:6](-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9])-[C:10]-[C:11]-1>>[O;D1;H0:8]=[C:7]1-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]2-[C:4]-[C:5]-[C:6]-1-[C:10]-[C:11]-2 | 97 | [{"value": 97.0, "product": "C12C(OC(C(CC1)CC2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "C12C(OC(C(CC1)CC2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2.9 g of cis-cyclohexane-1,4-dicarboxylic acid in 25 ml of acetic anhydride was heated under reflux for 2.5 hours. The solvent was removed by evaporation in vacuo, and the residue was triturated under diethyl ether several times. The residue was dried under high vacuum to give 2.5 g (97% yield) of the tit... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Anhydride | null | C1CC2CCC1COC2 | C1CC2CCC1COC2 | HO- | C(C)(=O)OC(C)=O | null | null | O=C(O)[C@@H]1CC[C@H](C(=O)O)CC1>C(C)(=O)OC(C)=O>O=C1OC(=O)C2CCC1CC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-60857aa3477447598ec3c7b21eeec7b1 | O=C(O)[C@@H]1CC[C@H](C(=O)O)C1>>O=C1OC(=O)C2CCC1C2 | [C@H]1(C[C@@H](CC1)C(=O)O)C(=O)O>>C12C(OC(C(CC1)C2)=O)=O | O[C:4](=[O:5])[C@@H:6]1[CH2:7][CH2:8][C@H:9]([C:2](=[O:1])[OH:3])[CH2:10]1>>[O:1]=[C:2]1[O:3][C:4](=[O:5])[CH:6]2[CH2:7][CH2:8][CH:9]1[CH2:10]2 | O=C(O)[C@@H]1CC[C@H](C(=O)O)C1 | O=C1OC(=O)C2CCC1C2 | null | null | C(C)(=O)OC(C)=O | Miscellaneous | OtherReaction | c1cea4e236c9cb0db48c718fcdbffddea16ce8c419b2e2e7c40ea0e652c0a082 | 22fb50577915472f1babb105381e408122dc09b3472eabb73e6e4daecfef90f6 | O=C1OC(=O)C2CCC1C2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@H;D3;+0:3]1-[C:4]-[C:5](-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8])-[C:9]-[C:10]-1>>[O;D1;H0:7]=[C:6]1-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]2-[C:4]-[C:5]-1-[C:9]-[C:10]-2 | 79 | [{"value": 79.0, "product": "C12C(OC(C(CC1)C2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "C12C(OC(C(CC1)C2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1.63 g of cis-cyclopentane-1,3-dicarboxylic acid in 8.2 ml of acetic anhydride was heated in an oil bath at ca. 100° C. for 45 minutes. The excess acetic anhydride and acetic acid were removed by evaporation in vacuo to give a solid which was triturated under diethyl ether. This afforded 1.14 g (79% yield... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Anhydride | null | C1CC2COCC1C2 | C1CC2COCC1C2 | HO- | C(C)(=O)OC(C)=O | null | null | O=C(O)[C@@H]1CC[C@H](C(=O)O)C1>C(C)(=O)OC(C)=O>O=C1OC(=O)C2CCC1C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-58c68fbf10174a44867b9854715d2022 | CC12CCC(CC1=O)C2(C)C>>CC12C=CC(CC1)C2(C)C | CC12C(CC(CC1)C2(C)C)=O.C[Li]>>CC12C=CC(CC1)C2(C)C | O=[C:3]1[C:2]2([CH3:1])[CH2:7][CH2:6][CH:5]([CH2:4]1)[C:8]2([CH3:9])[CH3:10]>>[CH3:1][C:2]12[CH:3]=[CH:4][CH:5]([CH2:6][CH2:7]1)[C:8]2([CH3:9])[CH3:10] | CC12CCC(CC1=O)C2(C)C | CC12C=CC(CC1)C2(C)C | null | null | CCOCC | Miscellaneous | OtherReaction | 4cb959f4e06d68c5567466f9e7266cf10d28d48a39d687cbffa44404f3d73067 | 9db0f73aed071f5fa7238b261fc87a241efa69e871d2f239452605149d0c954e | C1=CC2CCC1C2 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]2-[C:4]-[C:5]-[C:6]-1(-[C;D1;H3:7])-[C:8]-2>>[C;D1;H3:7]-[C:6]12-[C:5]-[C:4]-[C:3](-[C:8]-1)-[CH;D2;+0:2]=[CH;D2;+0:1]-2 | null | [] | null | null | null | null | 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one (1-camphor) was converted into its 4-toluenesulfonylhydrazone, which was then reacted with methyllithium in ether, to give the title compound. The method used was that described by Shapiro and Duncan, Organic Synthesis, Vol 51, pp 67-69, for the conversion of racemic camphor in... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CC2CCC1C2 | C1=CC2CCC1C2 | C1=CC2CCC1C2 | Other | CCOCC | null | null | CC12CCC(CC1=O)C2(C)C>CCOCC>CC12C=CC(CC1)C2(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a809adb031524620ae143b124d0bc36d | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1>>CN1CCC[C@H]1c1cccnc1 | C1CN(CCN1CCO)CCS(=O)(=O)O.NCCC1=CC(O)=C(O)C=C1.C1CN(CCN1CCO)CCS(=O)(=O)O.NCCC1=CC(O)=C(O)C=C1>>N1=CC=CC(=C1)[C@H]1N(C)CCC1 | N[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10](O)c(O)[cH:12]1.O=S(=O)(O)CCN1CC[N:11](CCO)CC1.O=S(=O)(O)CCN1CC[N:2]([CH2:1]CO)[CH2:3][CH2:4]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@H:6]1[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1 | CN1CCC[C@H]1c1cccnc1 | null | null | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O | Heteroatom Alkylation and Arylation | OtherReaction | 19fc9a872b549396d811b42e2ef2bc61edfc6ad753a9b784038fcb2d26d8bd1b | 22424af31acac19f7bdb5717c7b71b423c8772246143962540fd1af6bf911444 | c1cncc([C@@H]2CCCN2)c1 | N-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-O):c(-O):[cH;D2;+0:7]:1.O-C-C-[N;H0;D3;+0:8]1-C-C-N(-C-C-S(-O)(=O)=O)-C-C-1.O-C-[CH2;D2;+0:9]-[N;H0;D3;+0:10]1-C-C-N(-C-C-S(-O)(=O)=O)-[CH2;D2;+0:11]-[C:12]-1>>[CH3;D1;+0:9]-[N;H0;D3;+0:10]1-[C:12]-[CH2;D2;+0:11]-[CH2;D2;+0:1]-[C@H;D3;+0:2]-1-[c:3]1:[c:4]... | null | [] | null | null | 10 | MINUTE | Dopamine release was measured by preparing synaptosomes from the striatal area of rat brain obtained from Sprague-Dawley rats generally according to the procedures set forth by Nagy, et al., J. Neurochem., Vol. 43, pp. 1114-1123 (1984). Striata from 4 rats were homogenized in 2 ml of 0.32M sucrose buffered with 5 mM HE... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Aromatic alcohol.Aromatic alcohol.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine.Sulfonic acid.Sulfonic acid | Tertiary amine | c1ccccc1.C1CNCC[NH]1.C1CNCC[NH]1 | C1CC[NH]C1.c1ccncc1 | C1CC[NH]C1.c1ccncc1 | HO- | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O | null | 0.166667 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1>C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O>CN1CCC[C@H]1c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fa8c1a5973204abeab956b536c71aec8 | CC(=O)N1CCc2cc(Br)cc([N+](=O)[O-])c21>>CC(=O)N1CCc2cc(Br)cc(N)c21 | C(C)O.C(C)(=O)N1CCC2=CC(=CC(=C12)[N+](=O)[O-])Br.Cl>>C(C)(=O)N1CCC2=CC(=CC(=C12)N)Br | O=[N+:13]([O-])[c:12]1[cH:11][c:9]([Br:10])[cH:8][c:7]2[c:14]1[N:4]([C:2]([CH3:1])=[O:3])[CH2:5][CH2:6]2>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][c:12]([NH2:13])[c:14]21 | CC(=O)N1CCc2cc(Br)cc([N+](=O)[O-])c21 | CC(=O)N1CCc2cc(Br)cc(N)c21 | null | [Fe] | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)CCN2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]>>[#7:5]-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 32.2 | [{"value": 32.2, "product": "C(C)(=O)N1CCC2=CC(=CC(=C12)N)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.2, "product": "C(C)(=O)N1CCC2=CC(=CC(=C12)N)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixed solution of ethanol (400 ml) and water (100 ml), were added N-acetyl-5-bromo-7-nitroindoline (133.1 g), iron powder (10 mesh; 75 g) and concentrated hydrochloric acid (5 ml), and the mixture was subjected to refluxing for 5 hours with vigorous stirring. The reaction mixture was filtered by suction while hot ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CC[NH]2 | Other | [Fe].O | null | null | CC(=O)N1CCc2cc(Br)cc([N+](=O)[O-])c21>[Fe].O>CC(=O)N1CCc2cc(Br)cc(N)c21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-45f32967a0dc4124843cfe2d5c8768c7 | CC(=O)N1CCc2cc(Br)cc(N)c21.[C-]#N>>CC(=O)N1CCc2cc(Br)cc(C#N)c21 | C([O-])([O-])=O.[Na+].[Na+].[C-]#N.[Na+].Cl.C(C)(=O)N1CCC2=CC(=CC(=C12)N)Br.N(=O)[O-].[Na+]>>C(C)(=O)N1CCC2=CC(=CC(=C12)C#N)Br | N[c:12]1[cH:11][c:9]([Br:10])[cH:8][c:7]2[c:15]1[N:4]([C:2]([CH3:1])=[O:3])[CH2:5][CH2:6]2.[C-:13]#[N:14]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][c:12]([C:13]#[N:14])[c:15]21 | CC(=O)N1CCc2cc(Br)cc(N)c21.[C-]#N | CC(=O)N1CCc2cc(Br)cc(C#N)c21 | null | null | [Cu](C#N)C#N | C-C Coupling | OtherReaction | d194d4c4a9d9c9ec0fc04f5f7e6e0c048dcd771dea8c8ecf4b8d6b0ce492a143 | 6febc4a6ed64b39af6e5a12de3ade52adc549644adf3ef1f7265276b39762a0d | c1ccc2c(c1)CCN2 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[#7:6](-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[C:10].[C-;H0;D1:11]#[N;D1;H0:12]>>[C:10]-[#7:6](-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[c:4](:[c:5]):[c;H0;D3;+0:1](-[C;H0;D2;+0:11]#[N;D1;H0:12]):[c:2]:[c:3] | 81.1 | [{"value": 81.1, "product": "C(C)(=O)N1CCC2=CC(=CC(=C12)C#N)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.1, "product": "C(C)(=O)N1CCC2=CC(=CC(=C12)C#N)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -1 | CELSIUS | 30 | MINUTE | Into 6N hydrochloric acid (178.5 ml) was suspended N-acetyl-7-amino-5-bromoindoline (51.0 g), and aqueous solution (212 ml) of sodium nitrite (21.2 g) was dropwise added thereto under cooling with stirring over 30 minutes and at the inside temperature of not higher than -1° C. After stirred for 30 minutes at the temper... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Nitrile | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | Other | [Cu](C#N)C#N | -1 | 0.5 | CC(=O)N1CCc2cc(Br)cc(N)c21.[C-]#N>[Cu](C#N)C#N>CC(=O)N1CCc2cc(Br)cc(C#N)c21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-431b0132d8ae40649c3dfbbbb5dc0995 | CC(=O)N1CCc2cccc(C#N)c21.O=[N+]([O-])O>>CC(=O)N1CCc2cc([N+](=O)[O-])cc(C#N)c21 | S(O)(O)(=O)=O.[N+](=O)(O)[O-].C(C)(=O)N1CCC2=CC=CC(=C12)C#N>>C(C)(=O)N1CCC2=CC(=CC(=C12)C#N)[N+](=O)[O-] | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:13][c:14]([C:15]#[N:16])[c:17]21.O[N+:10](=[O:11])[O-:12]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]([C:15]#[N:16])[c:17]21 | CC(=O)N1CCc2cccc(C#N)c21.O=[N+]([O-])O | CC(=O)N1CCc2cc([N+](=O)[O-])cc(C#N)c21 | null | null | C(C)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 4e65a4adbea84d92823b0fafe885309e280190156042b1f4371c3e6c333fe875 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2c(c1)CCN2 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | 66.7 | [{"value": 66.7, "product": "C(C)(=O)N1CCC2=CC(=CC(=C12)C#N)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixed solution of acetic acid (3.8 ml), concentrated sulfuric acid (4.7 ml) and funing nitric acid (0.8 ml), under cooling with stirring, were added only small portions of N-acetyl-7-cyano-indoline (2.42 g). After stirred at the temperature as such for 7.5 hours, the reaction mixture was poured into ice-water (50 ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HO- | C(C)(=O)O | null | null | CC(=O)N1CCc2cccc(C#N)c21.O=[N+]([O-])O>C(C)(=O)O>CC(=O)N1CCc2cc([N+](=O)[O-])cc(C#N)c21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-00fe2cb189c24e55aa0d927376670bed | CC(=O)N1CCc2cc([N+](=O)[O-])cc(C#N)c21.[OH-]>>O=C(O)c1cc([N+](=O)[O-])cc2c1NCC2 | O.Cl.C(C)(=O)N1CCC2=CC(=CC(=C12)C#N)[N+](=O)[O-].[OH-].[Na+]>>[N+](=O)([O-])C=1C=C2CCNC2=C(C1)C(=O)O | CC(=[O:1])[N:13]1[c:12]2[c:4]([C:2]#N)[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]2[CH2:15][CH2:14]1.[OH-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]2[c:12]1[NH:13][CH2:14][CH2:15]2 | CC(=O)N1CCc2cc([N+](=O)[O-])cc(C#N)c21.[OH-] | O=C(O)c1cc([N+](=O)[O-])cc2c1NCC2 | null | null | null | Acylation | OtherReaction | ac3d65d9c53294f9973424968f809d052f81a2eaedb7e0ce5159ce4a1e0e9d0c | f8cddce93dd4493ccb430b4bb4fb38ac591294dc9ced3ff1c41fecd65dd89305 | c1ccc2c(c1)CCN2 | C-C(=[O;H0;D1;+0:1])-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7](-[C;H0;D2;+0:8]#N):[c:9].[OH-;D0:10]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:8](-[OH;D1;+0:10])-[c:7](:[c:9]):[c:6]1:[c:5]-[C:4]-[C:3]-[NH;D2;+0:2]-1 | 77.1 | [{"value": 77.1, "product": "[N+](=O)([O-])C=1C=C2CCNC2=C(C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 45 | MINUTE | Into concentrated hydrochloric acid (63.6 ml) was dissolved N-acetyl-7-cyano-5-nitroindoline (5.3 g), which was then subjected to stirring at 140° C. for 45 minutes. The reaction mixture was cooled to 0° C. to give deposited crystal, which was then collected by filtration. The obtained crude crystal was suspended into ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary amide | Carboxylic acid.Secondary amine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | null | 140 | 0.75 | CC(=O)N1CCc2cc([N+](=O)[O-])cc(C#N)c21.[OH-]>>O=C(O)c1cc([N+](=O)[O-])cc2c1NCC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-032ed9a94ceb4a87a0bff96b9f0cbbf6 | O=C(Cl)C(=O)Cl.c1ccc2c(c1)CCCCN2>>O=C1CCC2CCCc3ccn(c32)C1=O | C(C(=O)Cl)(=O)Cl.N1CCCCC2=C1C=CC=C2>>C1(C(CCC2CCCC=3C=CN1C23)=O)=O | Cl[C:2](=[O:1])[C:14](Cl)=[O:15].[CH2:3]1[CH2:4][c:5]2[cH:6][cH:7][cH:10][cH:9][c:13]2[NH:12][CH2:11][CH2:8]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]2[CH2:6][CH2:7][CH2:8][c:9]3[cH:10][cH:11][n:12]([c:13]32)[C:14]1=[O:15] | O=C(Cl)C(=O)Cl.c1ccc2c(c1)CCCCN2 | O=C1CCC2CCCc3ccn(c32)C1=O | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 2f46aba34cd265f2524bf18c42aff838dc68dbb40c378829428b5e2de9cdb8b4 | 54ad2df26383e81fa92b6fb9966ace45db4d93be43d5e6dfc90f2d8ecb91f1d6 | O=C1CCC2CCCc3ccn(c32)C1=O | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C:5]1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[NH;D2;+0:9]-[c:10]2:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15]:2-1>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH2;D2;+0:6]-[C:5]-[CH;D3;+0:15]2-[CH2;D2;+0:14]-[C... | null | [] | null | null | 4 | HOUR | To a solution of oxalic chloride (27.5 ml) in tetrahydrofuran (THF; 500 ml) which was subjected to refluxing with heating, was dropwise added a solution of 2,3,4,5-tetrahydro-1H-1-benzazepine (28.8 g) in THF (100 ml), which was thereafter subjected to stirring for 4 hours as such. After cooled, the solvent was distille... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Secondary amine | Ketone | c1ccc2c(c1)CCCCN2 | c1cn2c3c1CCCC3CCCC2 | c1cn2c3c1CCCC3CCCC2 | Other | O1CCCC1 | null | 4 | O=C(Cl)C(=O)Cl.c1ccc2c(c1)CCCCN2>O1CCCC1>O=C1CCC2CCCc3ccn(c32)C1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-53267f682d9a4174af11e039aaa24acc | BrCc1ccccc1.O=C(O)c1cc(Br)cc2c1NCCCC2>>O=C(OCc1ccccc1)c1cc(Br)cc2c1NCCCC2 | BrC=1C=C(C2=C(CCCCN2)C1)C(=O)O.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC(=O)C1=CC(=CC=2CCCCNC21)Br | Br[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[O:1]=[C:2]([OH:3])[c:11]1[cH:12][c:13]([Br:14])[cH:15][c:16]2[c:17]1[NH:18][CH2:19][CH2:20][CH2:21][CH2:22]2>>[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]([Br:14])[cH:15][c:16]2[c:17]1[NH:18][CH2:19][CH2:20][CH2:21][CH2:22]2 | BrCc1ccccc1.O=C(O)c1cc(Br)cc2c1NCCCC2 | O=C(OCc1ccccc1)c1cc(Br)cc2c1NCCCC2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(OCc1ccccc1)c1cccc2c1NCCCC2 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]>>[O;D1;H0:5]=[C:6](-[c:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 99.7 | [{"value": 99.7, "product": "C(C1=CC=CC=C1)OC(=O)C1=CC(=CC=2CCCCNC21)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 7-bromo-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid (8.53 g) dissolved in DMF (80 ml), were added potassium carbonate (13.8 g) and benzyl bromide (4.5 ml) and the mixture was stirred for 2 hours at room temperature. After the insoluble matter was filtered off and the filtrate was concentrated, a mixed liqu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccc2c(c1)CCCCN2 | HBr | CN(C)C=O | null | 2 | BrCc1ccccc1.O=C(O)c1cc(Br)cc2c1NCCCC2>CN(C)C=O>O=C(OCc1ccccc1)c1cc(Br)cc2c1NCCCC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ca2fd54a918b4c22a80531e0a6588ec9 | N#Cc1cc2c(c(C(=O)OCc3ccccc3)c1)NCCCC2.O.[OH-]>>O=C(O)c1cc2c(c(C(=O)O)c1)NCCCC2 | Cl.C(C1=CC=CC=C1)OC(=O)C1=CC(=CC=2CCCCNC21)C#N.[OH-].[Na+].O.C(C)O>>N1CCCCC2=C1C(=CC(=C2)C(=O)O)C(=O)O | N#[C:2][c:4]1[cH:5][c:6]2[c:7]([c:8]([C:9](=[O:10])[O:11]Cc3ccccc3)[cH:12]1)[NH:13][CH2:14][CH2:15][CH2:16][CH2:17]2.[OH2:1].[OH-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[c:7]([c:8]([C:9](=[O:10])[OH:11])[cH:12]1)[NH:13][CH2:14][CH2:15][CH2:16][CH2:17]2 | N#Cc1cc2c(c(C(=O)OCc3ccccc3)c1)NCCCC2.O.[OH-] | O=C(O)c1cc2c(c(C(=O)O)c1)NCCCC2 | null | null | O | Acylation | OtherReaction | b08f0680f444a5b98abc997dd17d8070d1520539f99f2ca0abbc5ed0361287c9 | a95e598260e5e8b2f09c862f84d42dd03f4b46fc2204cca4277e4958a9b5c4ff | c1ccc2c(c1)CCCCN2 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C-c1:c:c:c:c:c:1.[OH-;D0:9].[OH2;D0;+0:10]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[O;H0;D1;+0:10])-[OH;D1;+0:9]):[c:3] | 85 | [{"value": 85.0, "product": "N1CCCCC2=C1C(=CC(=C2)C(=O)O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Cyano-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid benzyl ester (3.30 g) and sodium hydroxide (2 g) in a mixed solution of water-ethanol (1:1, 60 ml) was refluxed for 8 hours. After cooled, water (100 ml) was added to the reaction mixture, which was then rendered to have pH 3 with concentrated hydrochloric a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrile | Carboxylic acid.Carboxylic acid | c1ccccc1 | null | c1ccc2c(c1)CCCCN2 | Other | O | null | null | N#Cc1cc2c(c(C(=O)OCc3ccccc3)c1)NCCCC2.O.[OH-]>O>O=C(O)c1cc2c(c(C(=O)O)c1)NCCCC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-caa6c7fdf4b245d7b6e59892ee5ce5b8 | CI.O=C(O)c1cc([N+](=O)[O-])cc2c1NCCCC2>>COC(=O)c1cc([N+](=O)[O-])cc2c1NCCCC2 | [N+](=O)([O-])C=1C=C(C2=C(CCCCN2)C1)C(=O)O.C([O-])([O-])=O.[K+].[K+].CI>>COC(=O)C1=CC(=CC=2CCCCNC21)[N+](=O)[O-] | I[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]2[c:13]1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18]2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]2[c:13]1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18]2 | CI.O=C(O)c1cc([N+](=O)[O-])cc2c1NCCCC2 | COC(=O)c1cc([N+](=O)[O-])cc2c1NCCCC2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccc2c(c1)CCCCN2 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 100.4 | [{"value": 100.4, "product": "COC(=O)C1=CC(=CC=2CCCCNC21)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 7-Nitro-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid (6.25 g) was dissolved into DMF (50 ml), to which then potassium carbonate (11 g) and methyl iodide (4.9 ml) were added, and was stirred for 2 hours at room temperature. After the insoluble matter was filtered off and the filtrate was concentrated, ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccc2c(c1)CCCCN2 | HI | CN(C)C=O | null | 2 | CI.O=C(O)c1cc([N+](=O)[O-])cc2c1NCCCC2>CN(C)C=O>COC(=O)c1cc([N+](=O)[O-])cc2c1NCCCC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d6f8a145407c4859b6e938637fa82e5b | CC(=O)O.CCOC(=O)Cc1csc(N)n1.CCOC=O>>CCOC(=O)C(C=O)c1csc(NC=O)n1 | C(C)(=O)O.NC=1SC=C(N1)CC(=O)OCC.[H-].[Na+].C(=O)OCC>>C(=O)C(C(=O)OCC)C=1N=C(SC1)NC=O | C[C:14](O)=[O:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:9]1[cH:10][s:11][c:12]([NH2:13])[n:16]1.CCO[CH:7]=[O:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH:7]=[O:8])[c:9]1[cH:10][s:11][c:12]([NH:13][CH:14]=[O:15])[n:16]1 | CC(=O)O.CCOC(=O)Cc1csc(N)n1.CCOC=O | CCOC(=O)C(C=O)c1csc(NC=O)n1 | null | null | CCCCCC.O1CCCC1 | C-C Coupling | OtherReaction | 3b5105526711349723848f369ec775fc4fed337a639e3b2f0269456627adcd50 | aa44f507ea5c97294be809c2851d03cb138387b764cc146bb1cb409c53ba7bff | c1cscn1 | C-C-O-[CH;D2;+0:1]=[O;D1;H0:2].C-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[c:10]1:[#7;a:11]:[c:12](-[NH2;D1;+0:13]):[#16;a:14]:[c:15]:1>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[CH;D2;+0:1]=[O;D1;H0:2])-[c:10]1:[#7;a:11]:[c:12](-[NH;D2;+0:13]-[CH;D2;+0:3]=[O;D1;H0:4]):[#16;a:... | null | [] | null | null | 18 | HOUR | Under nitrogen, 14 g (0.29 mmol) of 50% NaH in oil was washed with 2×40 ml of hexane and then suspended in 90 ml of anhydrous tetrahydrofuran (THF). To this slurry at 0° C. was added dropwise a solution of ethyl 2-(2-amino-4-thiazolyl)acetate (27 g, 0.145 mmol) in 290 ml of anhydrous THF, followed by ethyl formate (21.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ether.Primary amine | Aldehyde.Ester.Secondary amide | null | null | c1cscn1 | HO- | CCCCCC.O1CCCC1 | null | 18 | CC(=O)O.CCOC(=O)Cc1csc(N)n1.CCOC=O>CCCCCC.O1CCCC1>CCOC(=O)C(C=O)c1csc(NC=O)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-daf799bbc7ae46a8bc6b98336a253489 | O=C1CCCc2ccccc21.O=[N+]([O-])[O-]>>O=C1CCCc2c1cccc2[N+](=O)[O-] | C1CC2=CC=CC=C2C(=O)C1.[N+](=O)([O-])[O-].[K+]>>C1CC2=C(C=CC=C2[N+](=O)[O-])C(=O)C1 | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[c:7]1[cH:8][cH:9][cH:10][cH:11]2.O=[N+:12]([O-:13])[O-:14]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[c:7]1[cH:8][cH:9][cH:10][c:11]2[N+:12](=[O:13])[O-:14] | O=C1CCCc2ccccc21.O=[N+]([O-])[O-] | O=C1CCCc2c1cccc2[N+](=O)[O-] | null | null | CCOCC.S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with NO3 salt | 5993c528ef8bcdffbf8c0a893a552b598272f75e0f1825b53fb570da12e0cd5d | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C1CCCc2ccccc21 | O=[N+;H0;D3:1](-[O-;H0;D1:2])-[O;-;D1;H0:3].[C:4]-[c:5](:[c:6]-[C:7]=[O;D1;H0:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C:4]-[c:5](:[c:6]-[C:7]=[O;D1;H0:8]):[c;H0;D3;+0:9](-[N+;H0;D3:1](-[O;-;D1;H0:3])=[O;H0;D1;+0:2]):[c:10]:[c:11] | null | [] | null | null | null | null | 10 ml (75 mmol) of α-tetralone was added dropwise to 7.6 g (75 mmol) of potassium nitrate dissolved in 75 ml of concentrated sulfuric acid (at -10° C.). The resulting mixture was poured onto ice and the precipitate was suspended in ether. The precipitate (the 7 nitro isomer) was filtered off and the ether solution was ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | CCOCC.S(O)(O)(=O)=O | null | null | O=C1CCCc2ccccc21.O=[N+]([O-])[O-]>CCOCC.S(O)(O)(=O)=O>O=C1CCCc2c1cccc2[N+](=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-34ba7a5c0a8344839a71cd6270ce275f | BrBr.CN1Cc2ccc3c(c2C1)NC(=O)C3=O>>CN1Cc2c(Br)cc3c(c2C1)NC(=O)C3=O | CN1CC2=C(C1)C=CC1=C2NC(C1=O)=O.BrBr.C(=O)([O-])[O-].[Na+].[Na+]>>BrC1=CC2=C(NC(C2=O)=O)C=2CN(CC21)C | Br[Br:6].[CH3:1][N:2]1[CH2:3][c:4]2[cH:5][cH:7][c:8]3[c:9]([c:10]2[CH2:11]1)[NH:12][C:13](=[O:14])[C:15]3=[O:16]>>[CH3:1][N:2]1[CH2:3][c:4]2[c:5]([Br:6])[cH:7][c:8]3[c:9]([c:10]2[CH2:11]1)[NH:12][C:13](=[O:14])[C:15]3=[O:16] | BrBr.CN1Cc2ccc3c(c2C1)NC(=O)C3=O | CN1Cc2c(Br)cc3c(c2C1)NC(=O)C3=O | null | null | C(C)O.O | Functional Group Interconversion | Bromination | 024991405fc4a394b340e86799ec5211a4c48e8d63f6ade0a1282398db5744ea | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Nc2c(ccc3c2CNC3)C1=O | Br-[Br;H0;D1;+0:1].[#7:2]-[C:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]-[C:9]=[O;D1;H0:10]>>[#7:2]-[C:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[Br;H0;D1;+0:1]):[c:7]:[c:8]-[C:9]=[O;D1;H0:10] | null | [] | null | null | 5 | HOUR | To a stirred suspension of 1,6,7,8-tetrahydro-7-methylbenzo[2,1-b:3,4-c']dipyrrole-2,3-dione (0.5 g, 2.48 mmol) in water (20 ml) was added a solution of bromine (0.7 ml) in ethanol (5 ml). After 5 hours stirring at room temperature the reaction was completed and pH was adjusted to 8 with sat Na2CO3. The precipitated pr... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cc2c(c3c1C[NH]C3)NCC2 | c1cc2c(c3c1C[NH]C3)NCC2 | c1cc2c(c3c1C[NH]C3)NCC2 | HBr | C(C)O.O | null | 5 | BrBr.CN1Cc2ccc3c(c2C1)NC(=O)C3=O>C(C)O.O>CN1Cc2c(Br)cc3c(c2C1)NC(=O)C3=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-461d95d8d5924dfa90fb02af4201c163 | CN1CCc2c(ccc3c2NC(=O)C3=O)C1>>O=C1Nc2c(ccc3c2CCNC3)C1=O | CN1CC2=CC=C3C(=C2CC1)NC(C3=O)=O.ClC(C)OC(=O)Cl>>N1C(C(C=2C1=C1CCNCC1=CC2)=O)=O | C[N:12]1[CH2:11][CH2:10][c:9]2[c:4]3[c:5]([cH:6][cH:7][c:8]2[CH2:13]1)[C:14](=[O:15])[C:2](=[O:1])[NH:3]3>>[O:1]=[C:2]1[NH:3][c:4]2[c:5]([cH:6][cH:7][c:8]3[c:9]2[CH2:10][CH2:11][NH:12][CH2:13]3)[C:14]1=[O:15] | CN1CCc2c(ccc3c2NC(=O)C3=O)C1 | O=C1Nc2c(ccc3c2CCNC3)C1=O | null | null | ClCCCl | Deprotection | Hydrogenolysis of tertiary amines | 18419ec747aaa0e94571ae744ab97121176b8858419109d9f4c446bdba4c543e | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C1Nc2c(ccc3c2CCNC3)C1=O | C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[c:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[c:5] | null | [] | null | null | null | null | To an ice cooled stirred suspension of 6,7,8,9-tetrahydro-7-methyl-1H-pyrrolo[2,3-f]isoquinoline-2,3-dione (500 mg) in 1,2-dichloroethane (10 ml) was added α-chloroethylchloroformate (0.25 ml). The mixture was then brought to reflux for 1 hour, whereafter it was cooled to room temperature and filtered. The filtrate was... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1cc2c(c3c1C[NH]CC3)NCC2 | c1cc2c(c3c1CNCC3)NCC2 | c1cc2c(c3c1CNCC3)NCC2 | Other | ClCCCl | null | null | CN1CCc2c(ccc3c2NC(=O)C3=O)C1>ClCCCl>O=C1Nc2c(ccc3c2CCNC3)C1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1c632e8d02734363bc97532e616fc30a | CC(C)[C@@H](N)CO.COC(=O)Cl>>COC(=O)N[C@@H](CO)C(C)C | NCC(=O)O.C(C)N(CC)CC.N[C@H](C(C)C)CO.ClC(=O)OC>>COC(=O)N[C@H](C(C)C)CO | [NH2:5][C@@H:6]([CH2:7][OH:8])[CH:9]([CH3:10])[CH3:11].Cl[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]([CH2:7][OH:8])[CH:9]([CH3:10])[CH3:11] | CC(C)[C@@H](N)CO.COC(=O)Cl | COC(=O)N[C@@H](CO)C(C)C | null | null | C1CCOC1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6](-[C:7])-[NH2;D1;+0:8]>>[C:5]-[C:6](-[C:7])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | null | [] | -20 | CELSIUS | null | null | 39.7 g (0.385 mol) of D-valinol (Aldrich) are dissolved under nitrogen in 500 ml of dry THF. 58.7 ml (0.424 mol) of triethylamine are added, the mixture is cooled to -20° C. and 32.8 ml (0.424 mol) of methyl chloroformate (Aldrich) are added dropwise to the mixture with stirring. The mixture is subsequently stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | null | HCl | C1CCOC1 | -20 | null | CC(C)[C@@H](N)CO.COC(=O)Cl>C1CCOC1>COC(=O)N[C@@H](CO)C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-14e133718ef4419f957fbad21214f7e7 | COC(=O)N[C@@H](CO)C(C)C>>CC(C)[C@@H]1COC(=O)N1 | COC(=O)N[C@H](C(C)C)CO>>CC(C)[C@H]1NC(OC1)=O | CO[C:7](=[O:8])[NH:9][C@H:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][OH:6]>>[CH3:1][CH:2]([CH3:3])[C@@H:4]1[CH2:5][O:6][C:7](=[O:8])[NH:9]1 | COC(=O)N[C@@H](CO)C(C)C | CC(C)[C@@H]1COC(=O)N1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | Intramolecular transesterification/Lactone formation | d0b554db7a820dc59d151040a553cae8e3a26de1ed12e14eac9a9989c709d719 | be7fd34e803d2de455f5242fd01453ca257dbcbbaef3840c3cc1600f81a4a77c | O=C1NCCO1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C:5]-[OH;D1;+0:6]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[#7:3]-[C:4]-[C:5]-[O;H0;D2;+0:6]-1 | null | [] | 150 | CELSIUS | null | null | 27.2 g (168.7 mmol) of the compound from Example V are dissolved in 400 ml of toluene and stirred under reflux in an oil bath at 150° C. while passing in nitrogen.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary alcohol | Carbamic ester | null | C1COCN1 | C1COCN1 | HO- | C1(=CC=CC=C1)C | 150 | null | COC(=O)N[C@@H](CO)C(C)C>C1(=CC=CC=C1)C>CC(C)[C@@H]1COC(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9e0c26d35a4d43579f5bc9ade572d92d | CC(C)[C@H]1COC(=O)N1C(=O)CCc1ccccc1.O=Cc1ccccc1>>CC(C)[C@H]1COC(=O)N1C(=O)[C@H](Cc1ccccc1)[C@@H](O)c1ccccc1 | C(C1=CC=CC=C1)=O.C(C)(C)[N-]C(C)C.[Li+].C1(=CC=CC=C1)CCC(=O)N1C(OC[C@@H]1C(C)C)=O.[Cl-].[NH4+].C(CCC)[Li].C(C)(C)NC(C)C>>C(C1=CC=CC=C1)[C@@H](C(=O)N1C(OC[C@@H]1C(C)C)=O)[C@H](C1=CC=CC=C1)O | [CH3:1][CH:2]([CH3:3])[C@H:4]1[CH2:5][O:6][C:7](=[O:8])[N:9]1[C:10](=[O:11])[CH2:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH:20](=[O:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][CH:2]([CH3:3])[C@H:4]1[CH2:5][O:6][C:7](=[O:8])[N:9]1[C:10](=[O:11])[C@H:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][c... | CC(C)[C@H]1COC(=O)N1C(=O)CCc1ccccc1.O=Cc1ccccc1 | CC(C)[C@H]1COC(=O)N1C(=O)[C@H](Cc1ccccc1)[C@@H](O)c1ccccc1 | null | null | C1CCOC1.C(C)OCC | C-C Coupling | OtherReaction | 995c7a5cbf37230035b00de18cd91aae550f6b3916b2678b4c13427cfa9d9370 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | O=C1OCCN1C(=O)C(Cc1ccccc1)Cc1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8]-[c:9])-[C:10].[O;H0;D1;+0:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5](=[O;D1;H0:6])-[C@H;D3;+0:7](-[C:8]-[c:9])-[C@@H;D3;+0:12](-[OH;D1;+0:11])-[c:13](:[c:14]):[c:15])-[C:10] | null | [] | null | null | 1 | HOUR | 1.55 ml (11 mmol) of diisopropylamine is dissolved in 20 ml of absolute THF under argon and 7.75 ml (12 mmol) of n-butyllithium solution (1.55M in n-hexane, Aldrich) are added at -20° C. with stirring. The mixture is stirred at this temperature for 10 minutes and the freshly prepared solution of lithium diisopropylamid... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | C1COC[NH]1.c1ccccc1.c1ccccc1 | null | C1CCOC1.C(C)OCC | null | 1 | CC(C)[C@H]1COC(=O)N1C(=O)CCc1ccccc1.O=Cc1ccccc1>C1CCOC1.C(C)OCC>CC(C)[C@H]1COC(=O)N1C(=O)[C@H](Cc1ccccc1)[C@@H](O)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e7615e51d1964e48ab83367a353ca96f | CCOC(=O)C1CCNCC1.CCc1ccc(Br)nn1>>CCc1ccc(N2CCC(CO)CC2)nn1 | BrC=1N=NC(=CC1)CC.N1CCC(C(=O)OCC)CC1.C(C)(C)N(CC)C(C)C.CN1CCCC1>>C(C)C1=CC=C(N=N1)N1CCC(CC1)CO | CCO[C:11]([CH:10]1[CH2:9][CH2:8][NH:7][CH2:14][CH2:13]1)=[O:12].Br[c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[n:16][n:15]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([CH2:11][OH:12])[CH2:13][CH2:14]2)[n:15][n:16]1 | CCOC(=O)C1CCNCC1.CCc1ccc(Br)nn1 | CCc1ccc(N2CCC(CO)CC2)nn1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 077c674cc2e8fcc2fb5227831a1c9c99c9c1ca10677024dfb387b1bc25ec83f0 | 04c8bc1692f639277efb6482bc7a83b4782a3627dd0e275905c2bfb0e638743d | c1cnnc(N2CCCCC2)c1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.C-C-O-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[C:9]1-[C:10]-[C:11]-[N;H0;D3;+0:12](-[c;H0;D3;+0:1]2:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:2)-[C:13]-[C:14]-1 | null | [] | 140 | CELSIUS | 1 | HOUR | 1.67 g (0.011 mol) of 3-bromo-6-ethylpyridazine was added to 1.5 mL (10 mmol) ethyl isonipecotate and 3.5 mL (20 mmol) diisopropylethylamine and 5 mL N methylpyrrolidine (NMP). This mixture was heated to 140° C. for 4 hours. Upon cooling 100 mL of water was added to the mixture and the contents were extracted with meth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Secondary amine | Primary alcohol.Tertiary amine | C1CCNCC1.c1ccnnc1 | c1ccnnc1.C1CC[NH]CC1 | c1ccnnc1.C1CC[NH]CC1 | HBr | O | 140 | 1 | CCOC(=O)C1CCNCC1.CCc1ccc(Br)nn1>O>CCc1ccc(N2CCC(CO)CC2)nn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-61cb043d375d440baf6c30523544e136 | ClCc1ccccc1.N#Cc1ccc(O)cc1>>N#Cc1ccc(OCc2ccccc2)cc1 | O.C(#N)C1=CC=C(C=C1)O.C(C1=CC=CC=C1)Cl.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC1=CC=C(C#N)C=C1 | Cl[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:15][cH:16]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1 | ClCc1ccccc1.N#Cc1ccc(O)cc1 | N#Cc1ccc(OCc2ccccc2)cc1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | 95 | CELSIUS | 1.5 | HOUR | A mixture containing 325 g of 4-cyanophenol, 346 mL of benzyl chloride and 758 g of potassium carbonate in 1.2 L of NMP was heated at 95° C. with stirring for 1.5 hrs. The reaction mixture was cooled to room temperature and poured into 5 L of cold water. The resulting white solid was collected, washed with water and he... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | CN1CCCC1=O | 95 | 1.5 | ClCc1ccccc1.N#Cc1ccc(O)cc1>CN1CCCC1=O>N#Cc1ccc(OCc2ccccc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-da4ba2e333534753ac71b51a2ea124e5 | N#Cc1ccc(OCc2ccccc2)cc1.[N-]=[N+]=[N-]>>c1ccc(COc2ccc(-c3nnn[nH]3)cc2)cc1 | Cl.C(C1=CC=CC=C1)OC1=CC=C(C#N)C=C1.Cl.C(C)N(CC)CC.[N-]=[N+]=[N-].[Na+]>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1=NN=NN1 | [cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:16][cH:17]2)[cH:18][cH:19]1.[N-:13]=[N+:14]=[N-:15]>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[n:12][n:13][n:14][nH:15]3)[cH:16][cH:17]2)[cH:18][cH:19]1 | N#Cc1ccc(OCc2ccccc2)cc1.[N-]=[N+]=[N-] | c1ccc(COc2ccc(-c3nnn[nH]3)cc2)cc1 | null | null | CN(C)C=O.O | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(COc2ccc(-c3nnn[nH]3)cc2)cc1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[nH;D2;+0:3]:1):[c:9]:[c:10] | 98.1 | [{"value": 98.1, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1=NN=NN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 285 g of the nitrile, 262.5 g triethylamine hydrochloride and 124 g of sodium azide in 1.5 L of DMF under nitrogen was stirred under reflux for 18 hrs. The reaction mixture was cooled to room temperature, poured into 4 L of cold water and acidified with 3N HCl. The resulting white solid was collected, wash... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccccc1.c1ccccc1.c1nnn[nH]1 | null | CN(C)C=O.O | null | null | N#Cc1ccc(OCc2ccccc2)cc1.[N-]=[N+]=[N-]>CN(C)C=O.O>c1ccc(COc2ccc(-c3nnn[nH]3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-05c3ddf43a57421683e130c85cd4575d | CI.c1ccc(COc2ccc(-c3nnn[nH]3)cc2)cc1>>Cn1nnc(-c2ccc(OCc3ccccc3)cc2)n1 | CI.C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1=NN=NN1.CCN(C(C)C)C(C)C>>CN1N=C(N=N1)C1=CC=C(C=C1)OCC1=CC=CC=C1 | I[CH3:1].[nH:2]1[c:5](-[c:6]2[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19]2)[n:4][n:3][n:20]1>>[CH3:1][n:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19]2)[n:20]1 | CI.c1ccc(COc2ccc(-c3nnn[nH]3)cc2)cc1 | Cn1nnc(-c2ccc(OCc3ccccc3)cc2)n1 | null | null | O.CN1CCCC1=O | Heteroatom Alkylation and Arylation | OtherReaction | 930a6fb6aac3708578433b04494cf2b3154f49b6b8d322e37696a99afead7aa0 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(COc2ccc(-c3nn[nH]n3)cc2)cc1 | I-[CH3;D1;+0:1].[c:2]:[c:3](-[c;H0;D3;+0:4]1:[#7;a:5]:[n;H0;D2;+0:6]:[n;H0;D2;+0:7]:[nH;D2;+0:8]:1):[c:9]>>[CH3;D1;+0:1]-[n;H0;D3;+0:8]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:4](-[c:3](:[c:2]):[c:9]):[#7;a:5]:[n;H0;D2;+0:6]:1 | null | [] | 18 | CELSIUS | null | null | To a stirred solution containing 337 g of the tetrazole and 362 mL of DIPEA in 1 L of NMP cooled to 18° C. under N2 was added dropwise over 1.5 hrs 200 g of methyl iodide in 170 mL NMP. After stirring an additional hour at room temperature, the reaction mixture was diluted with 340 mL of water and the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1nnn[nH]1 | c1nnn[nH]1 | c1nnn[nH]1.c1ccccc1.c1ccccc1 | HI | O.CN1CCCC1=O | 18 | null | CI.c1ccc(COc2ccc(-c3nnn[nH]3)cc2)cc1>O.CN1CCCC1=O>Cn1nnc(-c2ccc(OCc3ccccc3)cc2)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3c595b8a98d54bcaa7886c6e9630ad8a | CCOC(=O)C1CCNCC1.Cc1ccc(Cl)nn1>>CCOC(=O)C1CCN(c2ccc(C)nn2)CC1 | CC1=CC=C(N=N1)Cl.N1CCC(C(=O)OCC)CC1>>C(=O)(OCC)C1CCN(CC1)C=1N=NC(=CC1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:17][CH2:18]1.Cl[c:10]1[cH:11][cH:12][c:13]([CH3:14])[n:15][n:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([CH3:14])[n:15][n:16]2)[CH2:17][CH2:18]1 | CCOC(=O)C1CCNCC1.Cc1ccc(Cl)nn1 | CCOC(=O)C1CCN(c2ccc(C)nn2)CC1 | null | null | C(C)(C)N(CC)C(C)C.CN1CCCC1=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75c7904d530fc47b0568d1a4c6ed822afd291ec9f7f11de72cd75ee4eb7d706d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cnnc(N2CCCCC2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1)-[C:10]-[C:11] | 44 | [{"value": 44.0, "product": "C(=O)(OCC)C1CCN(CC1)C=1N=NC(=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 55 mmoles of 6-methyl-3-chloropyridazine was added to 75 mmoles of ethyl isonipecotate in 5 mL NMP and 20 mL diisopropylethylamine (DIPEA) and refluxed for 6 hours. The product was isolated as described in Example 1a above to give a 44% yield of 3-(4-carboethoxy-1-piperidinyl)-6-methylpyridazine. Reduction of 18.8 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccnnc1 | C1CC[NH]CC1.c1ccnnc1 | C1CC[NH]CC1.c1ccnnc1 | HCl | C(C)(C)N(CC)C(C)C.CN1CCCC1=O | null | null | CCOC(=O)C1CCNCC1.Cc1ccc(Cl)nn1>C(C)(C)N(CC)C(C)C.CN1CCCC1=O>CCOC(=O)C1CCN(c2ccc(C)nn2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-497fa056f7bb46efa7e51c283e600987 | CCCc1ccc(N2CCC(O)CC2)nn1.Cc1cc(-c2nnn(C)n2)cc(C)c1O.Cc1cc(C#N)cc(C)c1O>>Cc1cc(-n2ncnn2)cc(C)c1O | C(CC)C1=CC=C(N=N1)N1CCC(CC1)O.C(CC)C1=CC=C(N=N1)N1CCC(CC1)O.CCOC(=O)/N=N/C(=O)OCC.CN1N=C(N=N1)C1=CC(=C(C(=C1)C)O)C.CN1N=C(N=N1)C1=CC(=C(C(=C1)C)O)C.CC1=C(C(=CC(=C1)C#N)C)O>>CC=1C=C(C=C(C1O)C)N1N=CN=N1.CN1N=C(N=N1)C1=CC(=C(C(=C1)C)O)C | CCCc1ccc([N:20]2CCC(O)CC2)[n:24]n1.Cc1cc(-c2nn(C)n[n:21]2)cc(C)c1O.[CH3:16][c:17]1[cH:18][c:19]([C:22]#[N:23])[cH:25][c:26]([CH3:27])[c:28]1[OH:29]>>[CH3:16][c:17]1[cH:18][c:19](-[n:20]2[n:21][cH:22][n:23][n:24]2)[cH:25][c:26]([CH3:27])[c:28]1[OH:29] | CCCc1ccc(N2CCC(O)CC2)nn1.Cc1cc(-c2nnn(C)n2)cc(C)c1O.Cc1cc(C#N)cc(C)c1O | Cc1cc(-n2ncnn2)cc(C)c1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0c7fbc8fe32c51cfe47637648a2f0cfa8a9c2e70567ddad2c7819252b9ca6158 | 3a4a9d0ecc5859ef1ddecc992f0568acf6c3d1a4a945d523e326b6396c3b4371 | c1ccc(-n2ncnn2)cc1 | C-C-C-c1:c:c:c(-[N;H0;D3;+0:1]2-C-C-C(-O)-C-C-2):[n;H0;D2;+0:2]:n:1.C-c1:c:c(-c2:[n;H0;D2;+0:3]:n:n(-C):n:2):c:c(-C):c:1-O.[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[n;H0;D3;+0:1]1:[n;H0;D2;+0:3]:[cH;D2;+0:5]:[n;H0;D2;+0:4]:[n;H0;D2;+0:2]:1):[c:9]:[c:10] | 71.9 | [{"value": 71.9, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Methyl-5-((3,5-dimethyl-4-hydroxyphenyl)-2H-tetrazole (Formula III: R2 =R3 =R4 =CH3) was prepared according to the procedure of Example 1b starting with 2,6-dimethyl-4-cyanophenol. 4.5 Mmol of 6-methyl-3-(4-hydroxyl-1-piperidinyl)pyridazine (Formula IV: R1 =methyl, Y=CH2), 1.14 g DEAD, 6.8 mmol TPP, 5 mmol of 2-methy... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary alcohol.Aromatic alcohol.Tertiary amine | null | c1ccnnc1.C1CC[NH]CC1.c1ccccc1.c1nnn[nH]1.c1ccccc1 | c1ccccc1.c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1 | HO- | null | null | null | CCCc1ccc(N2CCC(O)CC2)nn1.Cc1cc(-c2nnn(C)n2)cc(C)c1O.Cc1cc(C#N)cc(C)c1O>>Cc1cc(-n2ncnn2)cc(C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cddc616ecddf4bfb83a9be619ed5fcde | CCN(C(C)C)C(C)C.Cc1ccc(Br)nn1.OC1CCNCC1>>CCCc1ccc(N2CCC(O)CC2)nn1 | CC1=CC=C(N=N1)Br.CCN(C(C)C)C(C)C.OC1CCNCC1>>C(CC)C1=CC=C(N=N1)N1CCC(CC1)O | CC(C)N(C(C)C)[CH2:2][CH3:3].Br[c:7]1[cH:6][cH:5][c:4]([CH3:1])[n:16][n:15]1.[NH:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]1>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]2)[n:15][n:16]1 | CCN(C(C)C)C(C)C.Cc1ccc(Br)nn1.OC1CCNCC1 | CCCc1ccc(N2CCC(O)CC2)nn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0b64b87240d76137a9f4cb361727d91fdee39105ea0036bb365d641e2af39f18 | c9c3134d7b321cfb6c5863e4414081ce8b06e0bb826cc0f52b1792cb1bb1519c | c1cnnc(N2CCCCC2)c1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c;H0;D3;+0:4](-[CH3;D1;+0:5]):[c:6]:[c:7]:1.C-C(-C)-N(-[CH2;D2;+0:8]-[CH3;D1;+0:9])-C(-C)-C.[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c;H0;D3;+0:4](-[CH2;D2;+0:9]-[CH2;D2;+0:8]-[CH3;D1;+0:5]):[c:6]:[c:7]:1)-[C:13]-[... | null | [] | null | null | null | null | Following a procedure similar to that of Example 3, 81 millimoles of 6-methyl-3-bromopyridazine was combined with 16 mL DIPEA and 163 mmoles of 4-hydroxypiperidine and heated to 120° for 16 hours to obtain 6-methyl-3-(4-hydroxy-1-piperdinyl)pyridazine (Formula IV: Y=bond, R=CH3) in 24% yield. 6.8 Mmols of the latter an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Tertiary amine | Tertiary amine | c1ccnnc1.C1CCNCC1 | c1ccnnc1.C1CC[NH]CC1 | c1ccnnc1.C1CC[NH]CC1 | HBr | null | null | null | CCN(C(C)C)C(C)C.Cc1ccc(Br)nn1.OC1CCNCC1>>CCCc1ccc(N2CCC(O)CC2)nn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4bf57d14da074ba286dc99dcf47db4ab | CCOC(=O)Cc1ccncc1>>CCOC(=O)CC1CCNCC1 | N1=CC=C(C=C1)CC(=O)OCC.Cl>>N1CCC(CC1)CC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1 | CCOC(=O)Cc1ccncc1 | CCOC(=O)CC1CCNCC1 | null | [Pt]=O | [H][H].C(C)O | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1CCNCC1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[n;H0;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[CH;D3;+0:6]1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[NH;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1 | 162.3 | [{"value": 162.3, "product": "N1CCC(CC1)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 16.5 g (0.1 mol) Ethyl 4-pyridylacetate, 8.4 mL (0.1 mol) 12N hydrochloric acid and 2.5 g platinum oxide were dissolved in absolute ethanol and hydrogenated at 40 psi hydrogen on a Parr shaker. After 1 hour, the contents of the vessel were filtered and concentrated in vacuo yielding 27.79 g of ethyl 4-piperidinylacetat... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | C1CCNCC1 | null | [Pt]=O.[H][H].C(C)O | null | 1 | CCOC(=O)Cc1ccncc1>[Pt]=O.[H][H].C(C)O>CCOC(=O)CC1CCNCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6155d4e4a76d41d69a88452893850b2d | NCCNc1cccc(Cl)c1.O=C1CN2CCC1CC2>>Clc1cccc(NCCNC2CN3CCC2CC3)c1 | C(#N)[BH3-].[Na+].ClC=1C=C(C=CC1)NCCN.Cl.N12CC(C(CC1)CC2)=O.C(C)(=O)O>>N12CC(C(CC1)CC2)NCCNC2=CC(=CC=C2)Cl | [Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][NH2:10])[cH:19]1.O=[C:11]1[CH2:12][N:13]2[CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18]2>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][NH:10][CH:11]2[CH2:12][N:13]3[CH2:14][CH2:15][CH:16]2[CH2:17][CH2:18]3)[cH:19]1 | NCCNc1cccc(Cl)c1.O=C1CN2CCC1CC2 | Clc1cccc(NCCNC2CN3CCC2CC3)c1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 607e7f3018ab7c685429607eb463d325ac2961a41c4ff383d49bc2f5ec81fb78 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(NCCNC2CN3CCC2CC3)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[#7:3]2-[C:4]-[C:5]-[C:6]-1-[C:7]-[C:8]-2.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[CH;D3;+0:1]1-[C:2]-[#7:3]2-[C:4]-[C:5]-[C:6]-1-[C:7]-[C:8]-2 | 3.7 | [{"value": 3.7, "product": "N12CC(C(CC1)CC2)NCCNC2=CC(=CC=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of N-(3-chlorophenyl)-1,2-diaminoethane (1 g; 0,00586 moles) in 25 ml of anhydrous methanol kept under nitrogen atmosphere, 3-quinuclidinone hydrochloride (1.01 g, 0.0062? moles) is added. The pH is adjusted to pH 6 by addition of glacial acetic acid. Sodium cyanoborohydride (0.74 g; 0.0117 moles)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CN2CCC1CC2 | C1CN2CCC1CC2 | c1ccccc1.C1CN2CCC1CC2 | Other | CO | null | null | NCCNc1cccc(Cl)c1.O=C1CN2CCC1CC2>CO>Clc1cccc(NCCNC2CN3CCC2CC3)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-14c963ad2f0d4f1db8384f9ea0e1f629 | Clc1cccc(NCCNC2CN3CCC2CC3)c1.O=C(n1ccnc1)n1ccnc1>>Cl.O=C1N(c2cccc(Cl)c2)CCN1C1CN2CCC1CC2 | N12CC(C(CC1)CC2)NCCNC2=CC(=CC=C2)Cl.C1=CN(C=N1)C(=O)N2C=CN=C2>>Cl.N12CC(C(CC1)CC2)N2C(N(CC2)C2=CC(=CC=C2)Cl)=O | [Cl:1][c:9]1[cH:8][cH:7][cH:6][c:5]([NH:4][CH2:12][CH2:13][NH:14][CH:15]2[CH2:16][N:17]3[CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22]3)[cH:11]1.c1cn([C:3](n2ccnc2)=[O:2])cn1>>[ClH:1].[O:2]=[C:3]1[N:4]([c:5]2[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]2)[CH2:12][CH2:13][N:14]1[CH:15]1[CH2:16][N:17]2[CH2:18][CH2:19][CH:20]1[CH2:21... | Clc1cccc(NCCNC2CN3CCC2CC3)c1.O=C(n1ccnc1)n1ccnc1 | Cl.O=C1N(c2cccc(Cl)c2)CCN1C1CN2CCC1CC2 | null | null | O1CCCC1 | Acylation | OtherReaction | 22a00e38965c74658c7d990692fbfd3cd09eb841373095c6a6d9deab28a0178a | a568977d02e7655bdcf0c26df08c314b875d5aa4d39e583d0d214567d283a883 | O=C1N(c2ccccc2)CCN1C1CN2CCC1CC2 | [#7:1]-[C:2]-[C:3](-[NH;D2;+0:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[c:8]1:[c:9]:[c;H0;D3;+0:10](-[Cl;H0;D1;+0:11]):[c:12]:[c:13]:[c:14]:1)-[C:15].[O;D1;H0:16]=[C;H0;D3;+0:17](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[#7:1]-[C:2]-[C:3](-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[N;H0;D3;+0:7](-[c:8]2:[c:9]:[c;H0;D3;+0:10](-[Cl;D1;H0:18]):[c:12]:[c:13]:[c... | null | [] | null | null | null | null | To a stirred solution of N-(1-azabicyclo[2.2.2]oct-3 yl)-N'-(3-chlorphenyl)-1,2-diaminoethane (2.7 g; 0.0097 moles) in anhydrous tetrahydrofuran (10 ml), N,N-carbonyldiimidazole (2.04 g; 0.0125 moles) is added.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Secondary amine | Aromatic halide.Urea | c1ccccc1.c1c[nH]cn1.c1c[nH]cn1 | C1C[NH]C[NH]1.c1ccccc1 | C1C[NH]C[NH]1.c1ccccc1.C1CN2CCC1CC2 | Other | O1CCCC1 | null | null | Clc1cccc(NCCNC2CN3CCC2CC3)c1.O=C(n1ccnc1)n1ccnc1>O1CCCC1>Cl.O=C1N(c2cccc(Cl)c2)CCN1C1CN2CCC1CC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fb73d2cc67f846e59ed64d19ad23ad56 | COC(=O)c1ccc2[nH]cc(CCCCCl)c2c1.c1cc2c(cc1N1CCNCC1)OCCO2>>COC(=O)c1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | ClCCCCC1=CNC2=CC=C(C=C12)C(=O)OC.N1(CCNCC1)C1=CC2=C(OCCO2)C=C1>>COC(=O)C=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1 | Cl[CH2:15][CH2:14][CH2:13][CH2:12][c:11]1[cH:10][nH:9][c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:33][c:32]21.[NH:16]1[CH2:17][CH2:18][N:19]([c:20]2[cH:21][cH:22][c:23]3[c:24]([cH:25]2)[O:26][CH2:27][CH2:28][O:29]3)[CH2:30][CH2:31]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[nH:9][cH:10][c:11]([CH2:12... | COC(=O)c1ccc2[nH]cc(CCCCCl)c2c1.c1cc2c(cc1N1CCNCC1)OCCO2 | COC(=O)c1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c[nH]c2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | A solution of 3.6 g of 3-(4-chlorobutyl)-5-methoxycarbonylindole [obtainable by reaction of 5-methoxycarbonylindole with 4-chlorobutyryl chloride to give 3-(4-chlorobutyryl)-5-methoxy indole and subsequent reduction with diborane to give 3-(4-chlorobutyl)-5-methoxycarbonylindole] and 3.4 g of 6-piperazino-1,4-benzodiox... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | HCl | C(C)#N | null | null | COC(=O)c1ccc2[nH]cc(CCCCCl)c2c1.c1cc2c(cc1N1CCNCC1)OCCO2>C(C)#N>COC(=O)c1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6b2ca7d2d3694acca107a925b39fe209 | BrCCCCn1cnc2ccccc21.c1cc2c(cc1N1CCNCC1)OCCO2>>c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | BrCCCCN1C=NC2=C1C=CC=C2.N1(CCNCC1)C1=CC2=C(OCCO2)C=C1>>N1(C=NC2=C1C=CC=C2)CCCCN2CCN(CC2)C2=CC1=C(OCCO1)C=C2 | Br[CH2:13][CH2:12][CH2:11][CH2:10][n:9]1[c:4]2[cH:3][cH:2][cH:1][cH:6][c:5]2[n:7][cH:8]1.[NH:14]1[CH2:15][CH2:16][N:17]([c:18]2[cH:19][cH:20][c:21]3[c:22]([cH:23]2)[O:24][CH2:25][CH2:26][O:27]3)[CH2:28][CH2:29]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[n:7][cH:8][n:9]2[CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2... | BrCCCCn1cnc2ccccc21.c1cc2c(cc1N1CCNCC1)OCCO2 | c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | Analogously to Example 1, reaction of 1-(4-bromobutyl)benzimidazole with 6-piperazino-1,4-benzodioxane ("A") in 200 ml of acetonitrile gives 6-[4-(4-(benzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane, m.p. 247-248°.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2[nH]cnc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | HBr | C(C)#N | null | null | BrCCCCn1cnc2ccccc21.c1cc2c(cc1N1CCNCC1)OCCO2>C(C)#N>c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cd278516758a47cb98650ef6509a3367 | CCOC(=O)c1ccc2[nH]cc(CCCCN)c2c1.CCOC(=O)c1ccc2[nH]ccc2c1.O=C(Cl)CCCCl>>CCOC(=O)c1ccc2[nH]cc(CCCCCl)c2c1.CCOC(=O)c1ccc2[nH]cc(CCCCN3C(=O)c4ccccc4C3=O)c2c1.c1ccc2c(c1)OCCO2 | NCCCCC1=CNC2=CC=C(C=C12)C(=O)OCC.C(C)OC(=O)C=1C=C2C=CNC2=CC1.ClCCCC(=O)Cl>>ClCCCCC1=CNC2=CC=C(C=C12)C(=O)OCC.C1(C=2C(C(N1CCCCC1=CNC3=CC=C(C=C13)C(=O)OCC)=O)=CC=CC2)=O.O1CCOC2=C1C=CC=C2 | [CH3:13][CH2:21][O:22][C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]2[nH:29][cH:30][c:31]([CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])[c:47]2[cH:48]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[nH:10][cH:11][cH:12][c:18]2[cH:19]1.Cl[C:37](=[O:38])[CH2:39][CH2:44][CH2:45][Cl:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c... | CCOC(=O)c1ccc2[nH]cc(CCCCN)c2c1.CCOC(=O)c1ccc2[nH]ccc2c1.O=C(Cl)CCCCl | CCOC(=O)c1ccc2[nH]cc(CCCCCl)c2c1.CCOC(=O)c1ccc2[nH]cc(CCCCN3C(=O)c4ccccc4C3=O)c2c1.c1ccc2c(c1)OCCO2 | null | null | O.CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 1a558c634842dff071af490a9713caa3cc743947409d5b80cd06a7439e60b83f | b5a7bcb8d7299bda7a64520b8fc174825aa8a23a23c28a71eed01ef8288165f5 | O=C1c2ccccc2C(=O)N1CCCCc1c[nH]c2ccccc12.c1ccc2[nH]ccc2c1.c1ccc2c(c1)OCCO2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[Cl;H0;D1;+0:6].[CH3;D1;+0:7]-[CH2;D2;+0:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c:12].[C:13]-[C:14]-[NH2;D1;+0:15].[c:16]:[c:17]1:[cH;D2;+0:18]:[c:19]:[#7;a:20]:[c:21]:1:[c:22]>>[C;D1;H3:23]-[CH2;D2;+0:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c:12].[C:13]-[C:1... | null | [] | null | null | null | null | A mixture of 2.18 g of 3-(4-aminobutyl)-5-ethoxycarbonylindole [obtainable from 5-ethoxycarbonylindole by reaction with 4-chlorobutyryl chloride, reduction of the product to give 3-(4-chlorobutyl)-5-ethoxycarbonylindole and conversion into 3(4-phthalimidobutyl)-5-ethoxycarbonylindole] and one equivalent of 6-N,N-bis(2-... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Ester.Primary amine | Primary halide.Ester.Ether.Ether.Substituted dicarboximide | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)OCCO2 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1.c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)OCCO2 | null | O.CC(=O)C | null | null | CCOC(=O)c1ccc2[nH]cc(CCCCN)c2c1.CCOC(=O)c1ccc2[nH]ccc2c1.O=C(Cl)CCCCl>O.CC(=O)C>CCOC(=O)c1ccc2[nH]cc(CCCCCl)c2c1.CCOC(=O)c1ccc2[nH]cc(CCCCN3C(=O)c4ccccc4C3=O)c2c1.c1ccc2c(c1)OCCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-776d210858d547fca9d654d698089e84 | CCOC(=O)c1ccc2c(c1)ncn2CCCCN.ClCCN(CCCl)c1ccc2c(c1)OCCO2>>CCOC(=O)c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | NCCCCN1C=NC2=C1C=CC(=C2)C(=O)OCC.ClCCN(CCCl)C1=CC2=C(OCCO2)C=C1>>C(C)OC(=O)C1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[n:12][cH:13][n:14]2[CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].Cl[CH2:20][CH2:21][N:22]([c:23]1[cH:24][cH:25][c:26]2[c:27]([cH:28]1)[O:29][CH2:30][CH2:31][O:32]2)[CH2:33][CH2:34]Cl>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:1... | CCOC(=O)c1ccc2c(c1)ncn2CCCCN.ClCCN(CCCl)c1ccc2c(c1)OCCO2 | CCOC(=O)c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b3bf9675aff6ef0e1005a04072599878a79403b09607998b6a7d40fd8cc03d8c | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[CH2;D2;+0:5]-Cl.[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[N;H0;D3;+0:8]1-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[CH2;D2;+0:5]-1 | null | [] | null | null | null | null | Analogously to Example 3, reaction of 1-(4-aminobutyl)-5-ethoxycarbonylbenzimidazole with 6-(N,N-bis(2-chloroethyl)amino)-1,4-benzodioxane ("B") gives 6-[4(4-(5-ethoxycarbonylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1C[NH]CC[NH]1 | c1ccc2nc[nH]c2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CCOC(=O)c1ccc2c(c1)ncn2CCCCN.ClCCN(CCCl)c1ccc2c(c1)OCCO2>>CCOC(=O)c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-38db96a21eb54cbaaeba038afad9b60c | CC(=O)Cl.O=[N+]([O-])c1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1>>CC(=O)Nc1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | [N+](=O)([O-])C=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1.C(C)(=O)Cl>>C(C)(=O)NC=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1 | Cl[C:2]([CH3:1])=[O:3].O=[N+:4]([O-])[c:5]1[cH:6][cH:7][c:8]2[nH:9][cH:10][c:11]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][N:19]([c:20]4[cH:21][cH:22][c:23]5[c:24]([cH:25]4)[O:26][CH2:27][CH2:28][O:29]5)[CH2:30][CH2:31]3)[c:32]2[cH:33]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[nH:9][cH:10][c:11... | CC(=O)Cl.O=[N+]([O-])c1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | CC(=O)Nc1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | null | null | C1CCOC1 | Acylation | OtherReaction | f0304ee3e9240957ec5907301f002338c7115b9ed7ca824284b611a39e7511c3 | f8834895d54161280ecf6570c5eb4cac5e98229ebf3bc5a4595de2e3d57f4cd3 | c1ccc2c(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c[nH]c2c1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O=[N+;H0;D3:4](-[O-])-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 2 | HOUR | A solution of 4.21 g of 6-[4-(4-(5-aminoindol-3-yl)butyl)piperazino]-1,4-benzodioxane ("C") [obtainable as in Example 5] in 35 ml of THF is treated with a solution of 0.9 g of acetyl chloride in 10 ml of THF, and the mixture is stirred at 50° for 2 hours, evaporated and worked up in the conventional manner. 6-[4-(4-(5-... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Nitro group | Secondary amide | null | null | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | Other | C1CCOC1 | null | 2 | CC(=O)Cl.O=[N+]([O-])c1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1>C1CCOC1>CC(=O)Nc1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3e5d8cbf20784de7b4cf63b277ed7053 | CC(=O)Cl.Nc1ccc2ncn(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1>>CC(=O)Nc1ccc2ncn(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | NC=1C=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C1.C(C)(=O)Cl>>C(C)(=O)NC=1C=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C1 | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][N:19]([c:20]4[cH:21][cH:22][c:23]5[c:24]([cH:25]4)[O:26][CH2:27][CH2:28][O:29]5)[CH2:30][CH2:31]3)[c:32]2[cH:33]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11]([CH2:12... | CC(=O)Cl.Nc1ccc2ncn(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | CC(=O)Nc1ccc2ncn(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:9] | null | [] | null | null | null | null | Analogously to Example 6, reaction of 6-[4-(4-(6-aminobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane ("D") with acetyl chloride gives 6-[4-(4-(6-acetamidobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2[nH]cnc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CC(=O)Cl.Nc1ccc2ncn(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1>>CC(=O)Nc1ccc2ncn(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-263ca3ace86944b586055c5ed6138920 | CC(=O)Cl.Nc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1>>CC(=O)Nc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | NC1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1.C(C)(=O)Cl>>C(C)(=O)NC1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1 | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[n:11][cH:12][n:13]2[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][c:25]3[c:26]([cH:27]2)[O:28][CH2:29][CH2:30][O:31]3)[CH2:32][CH2:33]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[n:11][cH:1... | CC(=O)Cl.Nc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | CC(=O)Nc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:9] | null | [] | null | null | null | null | Analogously to Example 7, reaction of 6-[4-(4-(5-aminobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane ("E") with acetyl chloride gives 6-[4-(4-(5-acetamidobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2nc[nH]c2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CC(=O)Cl.Nc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1>>CC(=O)Nc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e38ff13a85fc45659c62ccbd6fef9407 | O=[N+]([O-])c1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1>>Nc1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | [N+](=O)([O-])C=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1>>NC=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][N:16]([c:17]4[cH:18][cH:19][c:20]5[c:21]([cH:22]4)[O:23][CH2:24][CH2:25][O:26]5)[CH2:27][CH2:28]3)[c:29]2[cH:30]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]3[CH2:14... | O=[N+]([O-])c1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | Nc1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c[nH]c2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A suspension of 3.8 g of 6-[4-(4-(5-nitroindol-3-yl)butyl)piperazino]-1,4-benzodioxane in 45 ml of methanol is hydrogenated with stirring on 0.1% Pd-C at 20° and 1 bar until absorption of H2 is complete. The mixture is poured into ice-water, worked up in the conventional manner and gives 6-[4-(4-(5-aminoindol-3-yl)buty... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | Other | [Pd].CO | null | null | O=[N+]([O-])c1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1>[Pd].CO>Nc1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a782508ad5da4e58a935bed7bb6cedd1 | CCOCCOCCO.N#Cc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1>>NC(=O)c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | C(#N)C1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1.[OH-].[Na+].C(C)OCCOCCO>>C(N)(=O)C1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1 | CCOCCOCC[OH:3].[N:1]#[C:2][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][cH:11][n:12]2[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][N:20]([c:21]2[cH:22][cH:23][c:24]3[c:25]([cH:26]2)[O:27][CH2:28][CH2:29][O:30]3)[CH2:31][CH2:32]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][cH:11][n:12]2[CH... | CCOCCOCCO.N#Cc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | NC(=O)c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 9176a763b26fae68fbe4845d484139261895801784506a90620ae7b690799339 | b47619e30802e158679368d096fd5212e62153e425ddf54cdc3440b6f3c12dcb | c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | C-C-O-C-C-O-C-C-[OH;D1;+0:1].[#7;a:2]:[c:3]:[c:4]:[c:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8]>>[#7;a:2]:[c:3]:[c:4]:[c:5](-[C;H0;D3;+0:6](-[NH2;D1;+0:7])=[O;H0;D1;+0:1]):[c:8] | null | [] | null | null | 3 | HOUR | A mixture of 4.16 g of 6-[4-(4-(5-cyanobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane, 2.4 g of NaOH, 50 ml of H2O and 40 ml of diethylene glycol monoethyl ether is stirred at a bath temperature of 140° for 3 hours. The mixture is then cooled to room temperature, worked up in the conventional manner and gives 6-[... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Nitrile.Primary alcohol | Primary amide | null | null | c1ccc2nc[nH]c2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | HO- | O | null | 3 | CCOCCOCCO.N#Cc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1>O>NC(=O)c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-22a8f936264443019aa427698e2e3d90 | COC(=O)c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1>>OCc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | [OH-].[Na+].N#N.[H-].[Al+3].[Li+].[H-].[H-].[H-].COC(=O)C1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1>>OCC1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][cH:10][n:11]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([c:20]2[cH:21][cH:22][c:23]3[c:24]([cH:25]2)[O:26][CH2:27][CH2:28][O:29]3)[CH2:30][CH2:31]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][cH:10][n:11]2[CH2:12][CH2:13][CH2:14... | COC(=O)c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | OCc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | null | null | 1 | HOUR | A solution of 4.4 g of 6-[4-(4-(5-methoxycarbonylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane in 40 ml of THF is added dropwise with stirring in an N2 atmosphere at 20° to a suspension of 0.6 g of lithium aluminium hydride in 20 ml of THF. The mixture is stirred at 20° for 1 hour, decomposed with dilute sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2nc[nH]c2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | Other | C1CCOC1 | null | 1 | COC(=O)c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1>C1CCOC1>OCc1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e8ab03e55e3649428504c580d6dadc51 | O=S(=O)(c1ccccc1)n1cc(CCCCN2CCN(c3ccc4c(c3)OCCO4)CC2)c2cc(Br)ccc21>>Brc1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | C1(=CC=CC=C1)S(=O)(=O)N1C=C(C2=CC(=CC=C12)Br)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1.[OH-].[K+]>>BrC=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1 | O=S(=O)(c1ccccc1)[n:6]1[c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:30][c:29]2[c:8]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19][c:20]4[c:21]([cH:22]3)[O:23][CH2:24][CH2:25][O:26]4)[CH2:27][CH2:28]2)[cH:7]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][CH2:12][N:13... | O=S(=O)(c1ccccc1)n1cc(CCCCN2CCN(c3ccc4c(c3)OCCO4)CC2)c2cc(Br)ccc21 | Brc1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | null | null | C(C)O | Reduction | OtherReaction | 0bdc206bc82b142c1f26c470803f0ffa0113e205282144abd9f91e21be64ca57 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc2c(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c[nH]c2c1 | O=S(=O)(-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[c:6])-c1:c:c:c:c:c:1>>[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | null | [] | null | null | null | null | 4.7 g of 6-[4-(4-(1-benzenesulfonyl-5-bromoindol-3-yl)butyl)piperazino]-1,4-benzodioxane is boiled for 16 hours with 1.5 g of KOH in aqueous ethanol solution, worked up in the conventional manner and gives 6-[4-(4-(5-bromoindol-3-yl)butyl)piperazino]-1,4-benzodioxane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | HO- | C(C)O | null | null | O=S(=O)(c1ccccc1)n1cc(CCCCN2CCN(c3ccc4c(c3)OCCO4)CC2)c2cc(Br)ccc21>C(C)O>Brc1ccc2[nH]cc(CCCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6c122948b65340e585059a9fd869a14c | CCOCCOCCO.N#Cc1ccc2[nH]cc(CCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1>>NC(=O)c1ccc2[nH]cc(CCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | C(#N)C=1C=C2C(=CNC2=CC1)CCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1.[OH-].[Na+].C(C)OCCOCCO>>C(N)(=O)C=1C=C2C(=CNC2=CC1)CCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1 | CCOCCOCC[OH:3].[N:1]#[C:2][c:4]1[cH:5][cH:6][c:7]2[nH:8][cH:9][c:10]([CH2:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][N:17]([c:18]4[cH:19][cH:20][c:21]5[c:22]([cH:23]4)[O:24][CH2:25][CH2:26][O:27]5)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][cH:9][c:10]([CH2:11][CH2:12][CH2:13][... | CCOCCOCCO.N#Cc1ccc2[nH]cc(CCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | NC(=O)c1ccc2[nH]cc(CCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 9176a763b26fae68fbe4845d484139261895801784506a90620ae7b690799339 | b47619e30802e158679368d096fd5212e62153e425ddf54cdc3440b6f3c12dcb | c1ccc2c(CCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c[nH]c2c1 | C-C-O-C-C-O-C-C-[OH;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 3 | HOUR | A mixture of 3.1 g of 6-[4-(3-(5-cyanoindol-3-yl)propyl)piperazino]-1,4-benzodioxane, 2.7 g of NaOH, 100 ml of water and 50 ml of diethylene glycol monoethyl ether is stirred at a bath temperature of 140° for 3 hours. It is cooled, worked up in the conventional manner and gives 6-[4-(3-(5-carbamoylindol-3-yl)propyl)pip... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Nitrile.Primary alcohol | Primary amide | null | null | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | HO- | O | null | 3 | CCOCCOCCO.N#Cc1ccc2[nH]cc(CCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1>O>NC(=O)c1ccc2[nH]cc(CCCN3CCN(c4ccc5c(c4)OCCO5)CC3)c2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2b73ef6cf0d74456b104b1399812863b | CCOC(=O)NN1CCC(c2cccc3ccccc23)CC1>>c1ccc2c(C3CCNCC3)cccc2c1 | C1(=CC=CC2=CC=CC=C12)C1CCN(CC1)NC(OCC)=O.Br>>Br.C1(=CC=CC2=CC=CC=C12)C1CCNCC1 | CCOC(=O)N[N:10]1[CH2:9][CH2:8][CH:7]([c:6]2[c:5]3[cH:4][cH:3][cH:2][cH:17][c:16]3[cH:15][cH:14][cH:13]2)[CH2:12][CH2:11]1>>[cH:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]3)[cH:13][cH:14][cH:15][c:16]2[cH:17]1 | CCOC(=O)NN1CCC(c2cccc3ccccc23)CC1 | c1ccc2c(C3CCNCC3)cccc2c1 | null | null | null | Reduction | Hydrogenolysis of tertiary amines | 988ed31d72828667c26978a5e403a8191844cdc865c4f2064419a2a4582ece30 | abe8486080f1db35588c5934c8ab05cddeada1638b7786a7f2ba894df44c1761 | c1ccc2c(C3CCNCC3)cccc2c1 | C-C-O-C(=O)-N-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 86.64 | [{"value": 86.64, "product": "Br.C1(=CC=CC2=CC=CC=C12)C1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 10.5 g of the compound obtained in Stage A in 300 ml of a 48% hydrobromic acid solution, are refluxed for 20 hours. After evaporation and washing twice with ethanol, the residue is taken up in acetone and the mixture then filtered to give 4-(naphth-1-yl)piperidine hydrobromide.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carbamic ester.Ether | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2ccccc2c1 | HO- | null | null | null | CCOC(=O)NN1CCC(c2cccc3ccccc23)CC1>>c1ccc2c(C3CCNCC3)cccc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c23b7acaed9b4fbbb249c32c51607fe4 | N#CCBr.c1ccc2c(C3CCNCC3)cccc2c1>>N#CCN1CCC(c2cccc3ccccc23)CC1 | Cl.Br.C1(=CC=CC2=CC=CC=C12)C1CCNCC1.C([O-])([O-])=O.[K+].[K+].BrCC#N>>Cl.C1(=CC=CC2=CC=CC=C12)C1CCN(CC1)CC#N | Br[CH2:4][C:3]#[N:2].[NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1>>[N:2]#[C:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | N#CCBr.c1ccc2c(C3CCNCC3)cccc2c1 | N#CCN1CCC(c2cccc3ccccc23)CC1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)cccc2c1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:7]-[C:8] | 91.83 | [{"value": 91.83, "product": "Cl.C1(=CC=CC2=CC=CC=C12)C1CCN(CC1)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5 g of the compound from Example 3, 7.088 g of potassium carbonate and 2.259 g of bromoacetonitrile in 200 ml of acetone are stirred for 10 hours under reflux and a stream of nitrogen. After filtering and evaporation of the filtrate, the residue obtained is treated with an ethanolic solution of hydrogen chloride to giv... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2ccccc2c1 | HBr | CC(=O)C | null | null | N#CCBr.c1ccc2c(C3CCNCC3)cccc2c1>CC(=O)C>N#CCN1CCC(c2cccc3ccccc23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2e907e16bf72484bb0b4699a8a7a2f7d | N#CCN1CCC(c2cccc3ccccc23)CC1>>NCCN1CCC(c2cccc3ccccc23)CC1 | [OH-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.C1(=CC=CC2=CC=CC=C12)C1CCN(CC1)CC#N.O.O>>NCCN1CCC(CC1)C1=CC=CC2=CC=CC=C12 | [N:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1>>[NH2:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1 | N#CCN1CCC(c2cccc3ccccc23)CC1 | NCCN1CCC(c2cccc3ccccc23)CC1 | null | null | O1CCCC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc2c(C3CCNCC3)cccc2c1 | [#7:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[#7:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | null | [] | null | null | 1 | HOUR | 1.75 g of lithium aluminum hydride are added in fractions under a stream of nitrogen to a solution of 4.4 g of the compound from Example 4 in 150 ml of tetrahydrofuran. After stirring for 1 hour, the mixture is hydrolyzed with 1.75 ml of water, 3.5 ml of a 10% (wt/wt) sodium hydroxide solution and 7 ml of water. Filtra... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CC[NH]CC1.c1ccc2ccccc2c1 | null | O1CCCC1 | null | 1 | N#CCN1CCC(c2cccc3ccccc23)CC1>O1CCCC1>NCCN1CCC(c2cccc3ccccc23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dbcee54bd5e04652bd5d90e8abadadc6 | Brc1cnc2ccccc2c1.CN1CCC(=O)CC1>>CN1CCC(O)(c2cnc3ccccc3c2)CC1 | BrC=1C=NC2=CC=CC=C2C1.C(CCC)[Li].CN1CCC(CC1)=O>>OC1(CCN(CC1)C)C=1C=NC2=CC=CC=C2C1 | Br[c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1.[CH3:1][N:2]1[CH2:3][CH2:4][C:5](=[O:6])[CH2:17][CH2:18]1>>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]([OH:6])([c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[cH:16]2)[CH2:17][CH2:18]1 | Brc1cnc2ccccc2c1.CN1CCC(=O)CC1 | CN1CCC(O)(c2cnc3ccccc3c2)CC1 | null | null | CCCCCC | C-C Coupling | Grignard_alcohol | 93eb5b8d9378b0ed52da86aa3c3f605c008f69dfc91c50beee4495359f07bb8c | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc2ncc(C3CCNCC3)cc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[O;H0;D1;+0:7]=[C;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:11]-[C:12]-[C:13]-1>>[OH;D1;+0:7]-[C;H0;D4;+0:8]1(-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-[C:9]-[C:10]-[#7:11]-[C:12]-[C:13]-1 | 53.84 | [{"value": 53.84, "product": "OC1(CCN(CC1)C)C=1C=NC2=CC=CC=C2C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 95.01 g of 3-bromoquinoline were treated with 200 ml of a 2.5M solution of butyllithium in hexane and 51.62 g of 1-methylpiperid-4-one in accordance with the procedure described in Stage A of Example 1, in order to obtain the expected product.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccc2ncccc2c1.C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | Br- | CCCCCC | null | null | Brc1cnc2ccccc2c1.CN1CCC(=O)CC1>CCCCCC>CN1CCC(O)(c2cnc3ccccc3c2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ad34ff3becb94a55b979a47c402aed39 | CN1CC=C(c2cnc3ccccc3c2)CC1>>C1=C(c2cnc3ccccc3c2)CCNC1 | Br.Br.CN1CCC(=CC1)C=1C=NC2=CC=CC=C2C1.Cl>>Cl.N1CCC(=CC1)C=1C=NC2=CC=CC=C2C1 | C[N:15]1[CH2:14][CH2:13][C:2]([c:3]2[cH:4][n:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[cH:12]2)=[CH:1][CH2:16]1>>[CH:1]1=[C:2]([c:3]2[cH:4][n:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[cH:12]2)[CH2:13][CH2:14][NH:15][CH2:16]1 | CN1CC=C(c2cnc3ccccc3c2)CC1 | C1=C(c2cnc3ccccc3c2)CCNC1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | 404caa5a14925901d5e54dc6d1a0a42a1eca30baa45d6e3c3549cb88842ef04f | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1=C(c2cnc3ccccc3c2)CCNC1 | C-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[c:5]:[c:6]:[#7;a:7])=[C:8]-[C:9]-1>>[#7;a:7]:[c:6]:[c:5]-[C:4]1=[C:8]-[C:9]-[NH;D2;+0:1]-[C:2]-[C:3]-1 | null | [] | null | null | null | null | This product was prepared from the compound of Example 7 and using the procedure described in Stages A and B of Example 6. The compound obtained was converted to a salt using an alcoholic solution of hydrogen chloride.
Conditions: See reaction.notes.procedure_details.
Workup: The compound obtained | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | C1=CC[NH]CC1 | C1=CCNCC1 | C1=CCNCC1.c1ccc2ncccc2c1 | Other | null | null | null | CN1CC=C(c2cnc3ccccc3c2)CC1>>C1=C(c2cnc3ccccc3c2)CCNC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1db42c7a9ca8429cb705dca7ff351e89 | COc1ccc2c(c1)C(O)(C1CCN(C)CC1)CCC2>>COc1ccc2c(c1)C(C1CCN(C)CC1)=CCC2 | OC1(CCCC2=CC=C(C=C12)OC)C1CCN(CC1)C.C1(=CC=C(C=C1)S(=O)(=O)O)C>>COC1=CC=C2CCC=C(C2=C1)C1CCN(CC1)C | O[C:9]1([CH:10]2[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]2)[c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[CH2:19][CH2:18][CH2:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)=[CH:17][CH2:18][CH2:19]2 | COc1ccc2c(c1)C(O)(C1CCN(C)CC1)CCC2 | COc1ccc2c(c1)C(C1CCN(C)CC1)=CCC2 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 55de719a68f8efde968ccdcfe54c921765e82cad5ee57c0bae7adf2d5c6460b3 | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | C1=C(C2CCNCC2)c2ccccc2CC1 | O-[C;H0;D4;+0:1]1(-[C:2](-[C:3])-[C:4])-[CH2;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10]>>[C:3]-[C:2](-[C;H0;D3;+0:1]1=[CH;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10])-[C:4] | null | [] | null | null | null | null | A solution of 15 g of the oil obtained in Stage A, in 400 ml of anhydrous dichloromethane, is refluxed for 20 minutes in the presence of 11.4 g of para-toluenesulfonic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1CC[NH]CC1.C1=Cc2ccccc2CC1 | HO- | ClCCl | null | null | COc1ccc2c(c1)C(O)(C1CCN(C)CC1)CCC2>ClCCl>COc1ccc2c(c1)C(C1CCN(C)CC1)=CCC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8e041e10770c49b4839e80c7837e0520 | COc1ccc2c(c1)C(C1CCN(C)CC1)=CCC2>>COc1ccc2cccc(C3CCN(C)CC3)c2c1 | COC1=CC=C2CCC=C(C2=C1)C1CCN(CC1)C.ClC1=C(C(=C(C(C1=O)=O)Cl)Cl)Cl>>COC1=CC=C2C=CC=C(C2=C1)C1CCN(CC1)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:18]([cH:19]1)[C:10]([CH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1)=[CH:9][CH2:8][CH2:7]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH:11]3[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]3)[c:18]2[cH:19]1 | COc1ccc2c(c1)C(C1CCN(C)CC1)=CCC2 | COc1ccc2cccc(C3CCN(C)CC3)c2c1 | null | null | null | Miscellaneous | OtherReaction | 93b4073d401b9871f39ba19f09d22c2607d954c2113d57f576b8550ecea6c3e1 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2c(C3CCNCC3)cccc2c1 | [C:1]-[C:2](-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]-1:[c:10])-[C:11]>>[C:1]-[C:2](-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10])-[C:11] | null | [] | null | null | null | null | A mixture of 11.5 g of the product from Example 15 and 23.1 g of tetrachloro-1,2-benzoquinone in solution in 600 ml of anhydrous ethyl acohol is refluxed for 30 hours.
Conditions: See reaction.notes.procedure_details.
Workup: is refluxed for 30 hours | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2ccccc2CC1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1.C1CC[NH]CC1 | null | null | null | null | COc1ccc2c(c1)C(C1CCN(C)CC1)=CCC2>>COc1ccc2cccc(C3CCN(C)CC3)c2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c53f731d9de94323887be2d52a3919fc | Brc1cccc2c1OCCO2.O=C1CCN(Cc2ccccc2)CC1>>OC1(c2cccc3c2OCCO3)CCN(Cc2ccccc2)CC1 | C(C1=CC=CC=C1)N1CCC(CC1)=O.C(CCC)[Li].BrC1=CC=CC=2OCCOC21.O>>C(C1=CC=CC=C1)N1CCC(CC1)(C1=CC=CC=2OCCOC21)O | Br[c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[O:9][CH2:10][CH2:11][O:12]2.[O:1]=[C:2]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[OH:1][C:2]1([c:3]2[cH:4][cH:5][cH:6][c:7]3[c:8]2[O:9][CH2:10][CH2:11][O:12]3)[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH... | Brc1cccc2c1OCCO2.O=C1CCN(Cc2ccccc2)CC1 | OC1(c2cccc3c2OCCO3)CCN(Cc2ccccc2)CC1 | null | null | CCCCCC.O1CCCC1 | C-C Coupling | Grignard_alcohol | 3bcd81d2e96d437e54160d37438c8b497fecd7254f0dccfc5a7f1bea7c0c2876 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(CN2CCC(c3cccc4c3OCCO4)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]-[#8:6])-[#8:7]-[C:8].[O;H0;D1;+0:9]=[C;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:13]-[C:14]-[C:15]-1>>[#8:6]-[c:5]:[c:4](:[c;H0;D3;+0:1](-[C;H0;D4;+0:10]1(-[OH;D1;+0:9])-[C:11]-[C:12]-[#7:13]-[C:14]-[C:15]-1):[c:2]:[c:3])-[#8:7]-[C:8] | null | [] | -60 | CELSIUS | 5 | MINUTE | 23.3 ml of a 1.6M solution of butyllithium in hexane are added dropwise to a solution, previously cooled to -60° C., of 8 g of 5-bromo-1,4-benzodioxane in 400 ml of tetrahydrofuran. When the addition is complete, the mixture is stirred at -60° C. for 5 minutes and a solution of 8 g of 1-benzylpiperid-4-one in 100 ml of... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccc2c(c1)OCCO2.C1CC[NH]CC1 | c1ccc2c(c1)OCCO2.C1CC[NH]CC1 | c1ccc2c(c1)OCCO2.C1CC[NH]CC1.c1ccccc1 | Br- | CCCCCC.O1CCCC1 | -60 | 0.083333 | Brc1cccc2c1OCCO2.O=C1CCN(Cc2ccccc2)CC1>CCCCCC.O1CCCC1>OC1(c2cccc3c2OCCO3)CCN(Cc2ccccc2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8836235aef454333bcb8b379cc7831d3 | C1=C(c2cccc3c2OCCO3)CCNC1.N#CCBr>>N#CCN1CC=C(c2cccc3c2OCCO3)CC1 | C([O-])([O-])=O.[K+].[K+].BrCC#N.Cl.O1CCOC2=C1C=CC=C2C=2CCNCC2>>O1CCOC2=C1C=CC=C2C=2CCN(CC2)CC#N | [NH:4]1[CH2:5][CH:6]=[C:7]([c:8]2[cH:9][cH:10][cH:11][c:12]3[c:13]2[O:14][CH2:15][CH2:16][O:17]3)[CH2:18][CH2:19]1.Br[CH2:3][C:2]#[N:1]>>[N:1]#[C:2][CH2:3][N:4]1[CH2:5][CH:6]=[C:7]([c:8]2[cH:9][cH:10][cH:11][c:12]3[c:13]2[O:14][CH2:15][CH2:16][O:17]3)[CH2:18][CH2:19]1 | C1=C(c2cccc3c2OCCO3)CCNC1.N#CCBr | N#CCN1CC=C(c2cccc3c2OCCO3)CC1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8654cc80599d789a53d1ba976beafc80caf5e8f4841be95ae420fabbb64ff19c | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1=C(c2cccc3c2OCCO3)CCNC1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[c:4]-[C:5]1=[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[C:5](-[c:4])=[C:6]-[C:7]-1 | null | [] | null | null | null | null | 2.5 g of potassium carbonate and, dropwise, a solution of 1.08 g of bromoacetonitrile in 10 ml of acetone are added to a solution of 1.9 g of the amine hydrochloride obtained in Stage B in 40 ml of acetone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1=CCNCC1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccc2c(c1)OCCO2 | HBr | CC(=O)C | null | null | C1=C(c2cccc3c2OCCO3)CCNC1.N#CCBr>CC(=O)C>N#CCN1CC=C(c2cccc3c2OCCO3)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-520e0e99ffeb4242aef88c01c7045ec3 | O=C1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1>>OC1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1 | S(=O)(=O)([O-])[O-].[Mg+2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(=CC=CC=C1)C(C1N2CCC(C1=O)CC2)C2=CC=CC=C2.[OH-].[Na+]>>C1(=CC=CC=C1)C(C1N2CCC(C1O)CC2)C2=CC=CC=C2 | [O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][N:6]([CH2:7][CH2:8]2)[CH:9]1[CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[OH:1][CH:2]1[CH:3]2[CH2:4][CH2:5][N:6]([CH2:7][CH2:8]2)[CH:9]1[CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=C1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1 | OC1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1 | null | null | O.O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | 927b703e99044128bba0275c9c21b6839b65333697fd637ab5168c5e4ff7694a | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(C(c2ccccc2)C2CC3CCN2CC3)cc1 | [C:1]-[C:2]1-[#7:3]2-[C:4]-[C:5]-[C:6](-[C:7]-[C:8]-2)-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10]>>[C:1]-[C:2]1-[#7:3]2-[C:4]-[C:5]-[C:6](-[C:7]-[C:8]-2)-[CH;D3;+0:9]-1-[OH;D1;+0:10] | null | [] | -65 | CELSIUS | 8 | HOUR | 2-(Diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-one (18.9 g) was dissolved in tetrahydrofuran (350 ml), anhydrous) and cooled to -65° C. under nitrogen. Lithium aluminium hydride (1.0 M solution in THF, 40 ml) was added dropwise to the solution which was stirred at room temperature overnight. Water (2 ml) followed by sod... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CN2CCC1CC2 | C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | null | O.O1CCCC1 | -65 | 8 | O=C1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1>O.O1CCCC1>OC1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2bbab0f4ae63457f992a8d6c141b0c62 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)c1cccc(I)c1>>CCc1cccc(C(=O)OC)c1 | [F-].[K+].IC=1C=C(C(=O)OC)C=CC1.C(=C)[Sn](CCCC)(CCCC)CCCC>>C(C)C=1C=C(C(=O)OC)C=CC1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].I[c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:12]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:12]1 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)c1cccc(I)c1 | CCc1cccc(C(=O)OC)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.O.C(C)(=O)OCC | C-C Coupling | OtherReaction | 4b5d1d49f48fb9361ff6f74e7f21d23798ac1391317b4153bbc2e1475cb17540 | a89dc659a2253daba9d05140816afc113af5c17adbf810ebb99d7455782f5ef3 | c1ccccc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:1]=[CH2;D1;+0:2].I-[c;H0;D3;+0:3](:[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9]:[c:10]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:3](-[CH2;D2;+0:1]-[CH3;D1;+0:2]):[c:9]:[c:10] | null | [] | null | null | 1 | DAY | Methyl 3-iodobenzoate (13 g) and vinyl tributyltin (20 g) were dissolved in toluene (100 ml) and tetrakis(triphenylphosphine)palladium (0) (500 mg) added. The solution was heated at reflux with stirring under N2 for 1 day. Potassium fluoride (3 g) in water (50 ml) was added and the reaction mixture was allowed to stir ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.O.C(C)(=O)OCC | null | 24 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)c1cccc(I)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.O.C(C)(=O)OCC>CCc1cccc(C(=O)OC)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d1c5882d2e4549bf91edac27d14b6d62 | C=Cc1cccc(CO)c1.ClC(Cl)(Cl)Cl>>C=Cc1cccc(CCl)c1 | C(=C)C=1C=C(CO)C=CC1.C(Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(=C)C=1C=C(CCl)C=CC1 | O[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([CH:2]=[CH2:1])[cH:10]1.ClC(Cl)(Cl)[Cl:9]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][Cl:9])[cH:10]1 | C=Cc1cccc(CO)c1.ClC(Cl)(Cl)Cl | C=Cc1cccc(CCl)c1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_Other | c7645f5879ae909e3b297fc6726e5b7253e918a949dafa12692ea59b390e5913 | cadad225bb90b3f5f5246e3c4efc1bc11b99bbdc1142f65854e2e6aa61cf93e1 | c1ccccc1 | Cl-C(-Cl)(-Cl)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 3-Ethenylbenzyl alcohol (5.26 g) was dissolved in carbon tetrachloride (100 ml) and triphenylphosphine (10.2 g) added. The solution was refluxed overnight and then left to cool. A white precipitate formed which was filtered through celite. The filtrate was evaporated in vacuo to yield a crude product. The residue was p... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Primary alcohol | Primary halide | null | null | c1ccccc1 | HCl | null | null | null | C=Cc1cccc(CO)c1.ClC(Cl)(Cl)Cl>>C=Cc1cccc(CCl)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6d347d740c6e4775b8e0120476bb6945 | O=C(c1ccccc1)c1ccccc1.O=C1CN2CCC1C2>>O=C1C2CCN(C2)C1C(O)(c1ccccc1)c1ccccc1 | Cl.N12CC(C(CC1)C2)=O.C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>C1(=CC=CC=C1)C(C1N2CCC(C1=O)C2)(O)C2=CC=CC=C2 | [C:9](=[O:10])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][N:6]([CH2:7]2)[CH2:8]1>>[O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][N:6]([CH2:7]2)[CH:8]1[C:9]([OH:10])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=C(c1ccccc1)c1ccccc1.O=C1CN2CCC1C2 | O=C1C2CCN(C2)C1C(O)(c1ccccc1)c1ccccc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 396c9454446273e86530db063ff6e6a3ee14e09093ce4c5aeee82c915e354a14 | 19b2c236afe469b02c86a8ce2284be8bbe6248fdfe9975ff6111471725b1daff | O=C1C2CCN(C2)C1C(c1ccccc1)c1ccccc1 | [C:1]-[#7:2]1-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-1.[O;H0;D1;+0:8]=[C;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[c:13](:[c:14]):[c:15]>>[C:1]-[#7:2]1-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[CH;D3;+0:7]-1-[C;H0;D4;+0:9](-[OH;D1;+0:8])(-[c:10](:[c:11]):[c:12])-[c:13](:[c:14]):[c:15] | null | [] | -78 | CELSIUS | 1 | HOUR | To a stirred mixture of 1-azabicyclo[2.2.1]heptan-3-one hydrochloride (1.06 g) and benzophenone (1.82 g) in dry THF (5 ml) at -78° C. under argon was added a solution of lithium bis(trimethylsilyl)amide (18 ml, 1.0M in THF). The solution was stirred at -78° C. for 1 h, allowed to warm to room temperature and stirred fo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone.Tertiary alcohol | C1CN2CCC1C2 | C1CN2CCC1C2 | C1CN2CCC1C2.c1ccccc1.c1ccccc1 | null | C1CCOC1 | -78 | 1 | O=C(c1ccccc1)c1ccccc1.O=C1CN2CCC1C2>C1CCOC1>O=C1C2CCN(C2)C1C(O)(c1ccccc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2296a711d5b9416e8708573c01ee1a3d | O=C1C2CCN(C2)C1C(O)(c1ccccc1)c1ccccc1>>OC1C2CCN(C2)C1C(O)(c1ccccc1)c1ccccc1 | S(=O)(=O)([O-])[O-].[Na+].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(=CC=CC=C1)C(C1N2CCC(C1=O)C2)(O)C2=CC=CC=C2.[OH-].[Na+]>>C1(=CC=CC=C1)C(C1N2CCC(C1O)C2)(O)C2=CC=CC=C2 | [O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][N:6]([CH2:7]2)[CH:8]1[C:9]([OH:10])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[OH:1][CH:2]1[CH:3]2[CH2:4][CH2:5][N:6]([CH2:7]2)[CH:8]1[C:9]([OH:10])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=C1C2CCN(C2)C1C(O)(c1ccccc1)c1ccccc1 | OC1C2CCN(C2)C1C(O)(c1ccccc1)c1ccccc1 | null | null | C1CCOC1.O | Reduction | Reduction of ketone to secondary alcohol | 82d6d639bc7e0467310eca4da3258252f2d2769053431b7090cd25512f803c65 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(C(c2ccccc2)C2CC3CCN2C3)cc1 | [C:1]-[C:2]1-[#7:3]2-[C:4]-[C:5]-[C:6](-[C:7]-2)-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[C:2]1-[#7:3]2-[C:4]-[C:5]-[C:6](-[C:7]-2)-[CH;D3;+0:8]-1-[OH;D1;+0:9] | null | [] | -78 | CELSIUS | 30 | MINUTE | 2-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-one (210 mg) was dissolved in THF (5 ml) at -78° C. under argon. Lithium aluminium hydride (3 ml, 1.0M in ether) was added and the mixture stirred at -78° C. for 30 min, and then warmed to room temperature whereupon the reaction mixture became homogeneous. Water (0.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CN2CCC1C2 | C1CN2CCC1C2 | C1CN2CCC1C2.c1ccccc1.c1ccccc1 | null | C1CCOC1.O | -78 | 0.5 | O=C1C2CCN(C2)C1C(O)(c1ccccc1)c1ccccc1>C1CCOC1.O>OC1C2CCN(C2)C1C(O)(c1ccccc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-247ca74c98124c71aa0d4daf168eb8af | O=C1CN2CCC1CC2.O=Cc1ccccc1Cl>>O=C1C(=Cc2ccccc2Cl)N2CCC1CC2 | N12CC(C(CC1)CC2)=O.ClC1=C(C=O)C=CC=C1.[OH-].[K+]>>ClC1=C(C=C2N3CCC(C2=O)CC3)C=CC=C1 | [O:1]=[C:2]1[CH2:3][N:12]2[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]2.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11]>>[O:1]=[C:2]1[C:3](=[CH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[Cl:11])[N:12]2[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]2 | O=C1CN2CCC1CC2.O=Cc1ccccc1Cl | O=C1C(=Cc2ccccc2Cl)N2CCC1CC2 | null | null | CO | C-C Coupling | Aldol condensation | 43a4150abc68ceec338b9cbb434168ffc350a154c35498f6bc5f681d8957435b | a6df440f86db37887787a8a1fbaac2563e9b43c193ca75024373eab7c3bfd6e5 | O=C1C(=Cc2ccccc2)N2CCC1CC2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[C:11]>>[C:5]-[#7:6](-[C:7])-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[C:11] | null | [] | null | null | null | null | 1-Azabicyclo[2.2.2]octan-3-one (3.86 g) was heated at reflux with 2-chlorobenzaldehyde (8.33 ml), potassium hydroxide (0.4 g) and methanol (60 ml) under nitrogen for 2.5 hours. The volatiles were removed in vacuo and the residue washed with sodium hydrogen carbonate. This was extracted (×4) with dichloromethane. The or... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Enamine | C1CN2CCC1CC2 | C1CN2CCC1CC2 | c1ccccc1.C1CN2CCC1CC2 | HO- | CO | null | null | O=C1CN2CCC1CC2.O=Cc1ccccc1Cl>CO>O=C1C(=Cc2ccccc2Cl)N2CCC1CC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-28e88db65242445cb373f341e46ba373 | O=C1C(=Cc2ccccc2Cl)N2CCC1CC2.[Br][Mg][c]1ccccc1>>O=C1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1Cl | ClC1=C(C=C2N3CCC(C2=O)CC3)C=CC=C1.C1(=CC=CC=C1)[Mg]Br>>ClC1=C(C=CC=C1)C(C1N2CCC(C1=O)CC2)C2=CC=CC=C2 | [O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][N:6]([CH2:7][CH2:8]2)[C:9]1=[CH:10][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[Cl:23].[Br][Mg][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][N:6]([CH2:7][CH2:8]2)[CH:9]1[CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21... | O=C1C(=Cc2ccccc2Cl)N2CCC1CC2.[Br][Mg][c]1ccccc1 | O=C1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1Cl | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 6e4f01870222ee8923caf8163945d9021501dd72bfe3aa0accb0f1a6426e3ad1 | 1796e631fda36d137ab7d9726a6bef311265a02183fdf5ad0ca709a48bb866ca | O=C1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[#7:14](-[C:15])-[C:16]>>[C:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[CH;D3;+0:10](-[c:11](:[c:12]):[c:13])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[#7:14](-[C:15])-[C:16] | null | [] | null | null | null | null | 2-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one (3 g) was dissolved in toluene (30 ml) and placed in a dropping funnel. Phenylmagnesium bromide was dissolved in toluene (15 ml) and stirred under nitrogen. This was cooled in an ice/water bath and the benzylidene solution was added dropwise. After 3 hrs the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Magnesium halide.Ketone | Ketone | c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | Br-.Mg | C1(=CC=CC=C1)C | null | null | O=C1C(=Cc2ccccc2Cl)N2CCC1CC2.[Br][Mg][c]1ccccc1>C1(=CC=CC=C1)C>O=C1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3709ccfe828b4265b38b3fb14b3078b9 | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O.O=C(OCc1ccccc1)[C@@H]1CCCN1>>CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1 | N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1.Cl.N([C@H](CC1=CC=CC=C1)C(=O)O)C(=O)OC(C)(C)C.CN1CCOCC1.C(C)N(CC)CC.ClC(=O)OCC(C)C>>N([C@H](CC1=CC=CC=C1)C(=O)N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1)C(=O)OC(C)(C)C | 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[C:24](=[O:25])[O:26][CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][c:1... | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O.O=C(OCc1ccccc1)[C@@H]1CCCN1 | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1 | null | null | C(Cl)(Cl)Cl.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(OCc1ccccc1)[C@@H]1CCCN1C(=O)CCc1ccccc1 | 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].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C:17]1-[C:18]-[C:19]-[C:20]-[NH;D2;+0:21]-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:... | 89.1 | [{"value": 89.1, "product": "N([C@H](CC1=CC=CC=C1)C(=O)N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Boc-(D)Phe-Pro-OH was produced by first preparing the dipeptide benzyl ester and then removing the ester by catalytic hydrogenation. Boc-(D)Phe-OH (10.0 g, 37.7 mmoles) was dissolved in 50 mL of THF and N-methylmorpholine (4.14 mL, 37.7 mmoles) was added. The solution was cooled to -20° and isobutyl chloroformate (4.90... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | C(Cl)(Cl)Cl.C1CCOC1 | null | 0.083333 | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O.O=C(OCc1ccccc1)[C@@H]1CCCN1>C(Cl)(Cl)Cl.C1CCOC1>CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-408c8484fe124834b5520e846e9adf68 | CC(=O)N[C@@H](C)C(=O)O.CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)O>>CC(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O | ON1C(CCC1=O)=O.N([C@@H](C)C(=O)O)C(=O)C.N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O.N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O.[OH-].[Na+].Cl.N([C@@H](C)C(=O)O)C(=O)C.C(C)N(CC)CC>>N([C@@H](C)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O)C(=O)C | O[C:7]([C@@H:5]([NH:4][C:2]([CH3:1])=[O:3])[CH3:6])=[O:8].[NH2:9][C@@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[C:23](=[O:24])[OH:25]>>[CH3:1][C:2](=[O:3])[NH:4][C@@H:5]([CH3:6])[C:7](=[O:8])[NH:9][C@@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])... | CC(=O)N[C@@H](C)C(=O)O.CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)O | CC(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O | null | null | O1CCOCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[O;D1;H1:14]>>[C:9]-[C:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:12](=[O;D1;H0:13])-[O;D1;H1:14] | null | [] | null | null | 8 | HOUR | Ac-Ala-Lys(Boc)-OH was prepared by coupling the N-hydroxysuccinimide ester of Ac-Ala-OH, prepared by the method of Anderson et al., J. Am. Chem. Soc. 86: 1839, (1964), to H-Lys(Boc)-OH. The N-hydroxy-succinimide of Ac-Ala-OH (6.25 g, 27.4 mmoles) was dissolved in 30 mL of dioxane and was added to a solution of H-Lys(Bo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | null | HO- | O1CCOCC1 | null | 8 | CC(=O)N[C@@H](C)C(=O)O.CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)O>O1CCOCC1>CC(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d330762a78a24610a29680bec14ad834 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1>>CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | N([C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C>>N([C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C.N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1 | [CH3:1][C:31]([CH3:3])([CH3:5])[O:30][C:28]([NH:6][C@@H:26]([CH2:25][CH:23]([CH3:22])[CH3:24])[C:35](=[O:36])[NH:37][C@@H:38]([CH3:39])[C:40](=[O:41])[O:42][CH2:43][c:44]1[cH:45][cH:46][cH:47][cH:48][cH:49]1)=[O:8]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH2:6])[C:7](=[O:8])[NH:9][C@@H:10]([CH3:11])[C:12](=[O:13])[O:14]... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | null | null | FC(C(=O)O)(F)F | Aromatic Heterocycle Formation | Hydrogenolysis of amides/imides/carbamates | 24737001e4f03821c8e91589c46a8bbcd4ae511ea943cdd7e11b75a61b037d65 | a65947919efc48e3162572af35f1d8ac3527467df7e5e89fdb96913dba22a467 | c1ccccc1.c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C@H;D3;+0:8](-[C:9]-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[#8:14]-[C;H0;D4;+0:15](-[CH3;D1;+0:16])(-[CH3;D1;+0:17])-[CH3;D1;+0:18]>>[#7:19]-[C:20](=[O;H0;D1;+0:13])-[C@@H;D3;+0:18](-[NH2;D1;+0:11])-[C:21]-[C:22](-[CH3;D1;+0:16])-[CH3;D1;+0:1... | null | [] | null | null | 15 | MINUTE | Boc-Leu-Ala-OBzl was prepared by the procedure for dipeptide synthesis in Example 2. Boc-Leu-Ala-OBzl (23.7 g, 57.7 mmoles) was dissolved in 40 mL of anhydrous trifluoroacetic acid. After 15 min, excess trifluoroacetic acid was removed by evaporation and the residue was treated with ether to yield H-Leu-Ala-OBzl.triflu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Carbamic ester.Ester.Ether.Secondary amide.Primary amine.Boc | null | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | FC(C(=O)O)(F)F | null | 0.25 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1>FC(C(=O)O)(F)F>CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e95bb68602144d5c8b548570c446fb1d | CC(C)(C)OC(=O)NCC(=O)O.CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1>>CC(C)C[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | N(CC(=O)O)C(=O)OC(C)(C)C.N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1>>N(CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C | O[C:7](=[O:8])[CH2:9][NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH2:6])[C:18](=[O:19])[NH:20][C@@H:21]([CH3:22])[C:23](=[O:24])[O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[CH2:9][NH:10][C:11]... | CC(C)(C)OC(=O)NCC(=O)O.CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | CC(C)C[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]-[#7:16]-[C:17](=[O;D1;H0:18])-[C:19](-[C:20])-[NH2;D1;+0:21]>>[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]-[#7:16]-[C:17](=[O;D1;H0:18])-[C:19](-[C:20])-[NH;D2;+0:21]-[C;H0... | null | [] | null | null | null | null | Boc-Gly-Leu-Ala-OBzl was prepared by coupling Boc-Gly-OH (5.70 g, 32.6 mmoles) to H-Leu-Ala-OBzl using the mixed anhydride procedure described in Example 2. The product (13.8 g) was obtained as an amorphous solid. Boc-Gly-Leu-Ala-OBzl was deblocked with trifluoroacetic acid by the procedure described for the preparatio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)NCC(=O)O.CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1>>CC(C)C[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1e9e6ea312024abbb5827b12a87dd34a | CC(C)C[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1>>CC(C)C[C@H](NC(=O)CN)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | N(CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C.FC(C(=O)O)(F)F.N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1.FC(C(=O)[O-])(F)F.Cl>>NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1.Cl | CC(C)(C)OC(=O)[NH:10][CH2:9][C:7]([NH:6][C@@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:11](=[O:12])[NH:13][C@@H:14]([CH3:15])[C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)=[O:8]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[CH2:9][NH2:10])[C:11](=[O:12])[NH:13][C@@H:14]([CH3:15])[C:16]... | CC(C)C[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | CC(C)C[C@H](NC(=O)CN)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | null | null | CCOCC.C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]-[C:7](-[#7:8])=[O;D1;H0:9]>>[#7:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | Boc-Gly-Leu-Ala-OBzl was prepared by coupling Boc-Gly-OH (5.70 g, 32.6 mmoles) to H-Leu-Ala-OBzl using the mixed anhydride procedure described in Example 2. The product (13.8 g) was obtained as an amorphous solid. Boc-Gly-Leu-Ala-OBzl was deblocked with trifluoroacetic acid by the procedure described for the preparatio... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | CCOCC.C(C)(=O)OCC | null | null | CC(C)C[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1>CCOCC.C(C)(=O)OCC>CC(C)C[C@H](NC(=O)CN)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dcb3efb5c2714b649c6024418e3d449a | CC(C)C[C@H](NC(=O)CN)C(=O)N[C@@H](C)C(=O)OCc1ccccc1.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O>>CC(C)C[C@H](NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | N([C@@H](CC(C)C)C(=O)O)C(=O)OC(C)(C)C.NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1>>N([C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[CH2:9][NH2:10])[C:26](=[O:27])[NH:28][C@@H:29]([CH3:30])[C:31](=[O:32])[O:33][CH2:34][c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1.O[C:11](=[O:12])[C@H:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25]>>[CH3:1][CH:... | CC(C)C[C@H](NC(=O)CN)C(=O)N[C@@H](C)C(=O)OCc1ccccc1.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O | CC(C)C[C@H](NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | 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].[#7:13]-[C:14](=[O;D1;H0:15])-[C:16]-[#7:17]-[C:18](=[O;D1;H0:19])-[C:20]-[NH2;D1;+0:21]>>[#7:13]-[C:14](=[O;D1;H0:15])-[C:16]-[#7:17]-[C:18](=[O;D1;H0:19])-[C:20]-[NH;D2;+0:21]-[C;H0;D3;+0:1]... | null | [] | null | null | null | null | Boc-Leu-Gly-Leu-Ala-OBzl was prepared by coupling Boc-Leu-OH (2.62 g, 10.5 mmoles) to H-Gly-Leu-Ala-OBzl using the mixed anhydride procedure described in Example 2. The resulting product was crystallized from ethyl acetate:hexane to yield 2.7 g (mp 95°-96°) in the first crop.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | null | null | null | CC(C)C[C@H](NC(=O)CN)C(=O)N[C@@H](C)C(=O)OCc1ccccc1.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O>>CC(C)C[C@H](NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-546e985c373d49ba8a1bca6b63eaccc9 | CC(=O)Nc1nnc(S(N)(=O)=O)s1>>Nc1nnc(S(N)(=O)=O)s1 | Cl.C(C)(=O)NC=1SC(=NN1)S(=O)(=O)N.C(C)(=O)N.CC(=O)NC1=NN=C(S1)S(=O)(=O)N.Cl>>NC=1SC(=NN1)S(=O)(=O)N | CC(=O)[NH:1][c:2]1[n:3][n:4][c:5]([S:6]([NH2:7])(=[O:8])=[O:9])[s:10]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([S:6]([NH2:7])(=[O:8])=[O:9])[s:10]1 | CC(=O)Nc1nnc(S(N)(=O)=O)s1 | Nc1nnc(S(N)(=O)=O)s1 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1nncs1 | C-C(=O)-[NH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[#7;a:6]:1>>[NH2;D1;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[#7;a:6]:1 | 85 | [{"value": 85.0, "product": "NC=1SC(=NN1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | This is prepared by hydrolysis of the acetamide 2-acetylamino-1,3,4-thiadiazole-5-sulfonamide (acetazolamide). A slurry of 0.2 mol of acetazolamide in 600 mL of methanol is treated with 60 mL 12N HCl. This mixture is heated with stirring to reflux for 6 hours. Reaction progress is monitored using liquid chromatography.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1nncs1 | HO- | CO | null | 6 | CC(=O)Nc1nnc(S(N)(=O)=O)s1>CO>Nc1nnc(S(N)(=O)=O)s1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-acac8f88fae84d0d92a648b8d5b90be2 | CC(=O)OC(C)=O.CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1>>CC(=O)CC(=O)O.CC(=O)[O-] | C(C)(=O)OC(C)=O.C[C@@H]1/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)O[C@@H]1C(C)C)O)/C>>CC(=O)[O-].CC(=O)CC(=O)O | [CH3:4][C:5](=[O:6])[O:7][C:9]([CH3:8])=[O:10].CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c2coc(n2)CC(=[O:3])C[C@H](O)/C=[C:2]([CH3:1])/C=C/CNC(=[O:11])/C=C/[C@H]1C>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[OH:7].[CH3:8][C:9](=[O:10])[O-:11] | CC(=O)OC(C)=O.CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1 | CC(=O)CC(=O)O.CC(=O)[O-] | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | 34004ef5ba7f397795c3b399bd0e151cef344af1e1499a8505b14abf9c824187 | c692c8eb979187b14593ec4d98b5f03ea7f501cb755700ee2ec4bd07e01eab71 | null | C-C(-C)-[C@@H]1-O-C(=O)-C2=C-C-C-N-2-C(=O)-c2:c:o:c(:n:2)-C-C(=[O;H0;D1;+0:1])-C-[C@H](-O)/C=[C;H0;D3;+0:2](-[C;D1;H3:3])/C=C/C-N-C(=[O;H0;D1;+0:4])/C=C/[C@@H]-1-C.[C;D1;H3:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[C:9](-[CH3;D1;+0:10])=[O;D1;H0:11]>>[C;D1;H3:5]-[C;H0;D3;+0:6](-[O-;H0;D1:4])=[O;D1;H0:7].[C;D1;H3:... | null | [] | null | null | 30 | MINUTE | Acetic anhydride (45 ml) was added to a stirring solution of Virginiamycin M1 (6.5 g) in anhydrous pyridine (45 ml) at room temperature. After 30 minutes, ice-cold methanol (85 ml) was added in portions. Stirring was continued for 20 more minutes followed by flash evaporation to dryness at room temperature. The residue... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Anhydride.Ketone.Ester.Secondary amide.Tertiary amide.Secondary alcohol | Carboxylic acid.Ketone | C1=C2COCC/C=C/CNC/C=C/C=C/CCCCc3nc(co3)CN2CC1 | null | null | HO- | N1=CC=CC=C1 | null | 0.5 | CC(=O)OC(C)=O.CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1>N1=CC=CC=C1>CC(=O)CC(=O)O.CC(=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0d147c8237e642a6a930435c14340e40 | CC(=O)OC(C)=O.CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1>>CC(=O)CC(=O)O.CC(=O)[O-] | C(C)(=O)OC(C)=O.C[C@@H]1/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)O[C@@H]1C(C)C)O)/C>>CC(=O)[O-].CC(=O)CC(=O)O | [CH3:4][C:5](=[O:6])[O:7][C:9]([CH3:8])=[O:10].CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c2coc(n2)CC(=[O:3])C[C@H](O)/C=[C:2]([CH3:1])/C=C/CNC(=[O:11])/C=C/[C@H]1C>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[OH:7].[CH3:8][C:9](=[O:10])[O-:11] | CC(=O)OC(C)=O.CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1 | CC(=O)CC(=O)O.CC(=O)[O-] | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | 34004ef5ba7f397795c3b399bd0e151cef344af1e1499a8505b14abf9c824187 | c692c8eb979187b14593ec4d98b5f03ea7f501cb755700ee2ec4bd07e01eab71 | null | C-C(-C)-[C@@H]1-O-C(=O)-C2=C-C-C-N-2-C(=O)-c2:c:o:c(:n:2)-C-C(=[O;H0;D1;+0:1])-C-[C@H](-O)/C=[C;H0;D3;+0:2](-[C;D1;H3:3])/C=C/C-N-C(=[O;H0;D1;+0:4])/C=C/[C@@H]-1-C.[C;D1;H3:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[C:9](-[CH3;D1;+0:10])=[O;D1;H0:11]>>[C;D1;H3:5]-[C;H0;D3;+0:6](-[O-;H0;D1:4])=[O;D1;H0:7].[C;D1;H3:... | null | [] | null | null | 30 | MINUTE | Acetic anhydride (45 ml) was added to a stirring solution of Virginiamycin M1 (6.5 g) in anhydrous pyridine (45 ml) at room temperature. After 30 minutes, ice-cold methanol (85 ml) was added in portions. Stirring was continued for 20 more minutes followed by flash evaporation to dryness at room temperature. The residue... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Anhydride.Ketone.Ester.Secondary amide.Tertiary amide.Secondary alcohol | Carboxylic acid.Ketone | C1=C2COCC/C=C/CNC/C=C/C=C/CCCCc3nc(co3)CN2CC1 | null | null | HO- | N1=CC=CC=C1 | null | 0.5 | CC(=O)OC(C)=O.CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1>N1=CC=CC=C1>CC(=O)CC(=O)O.CC(=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-30559a06ff8749fdb1c766b31f5aecc9 | CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1.O=C(Cl)Cl.c1ccncc1>>CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1.CCCCC(=O)O.O=C([O-])c1ccccc1 | C(=O)(Cl)Cl.C[C@@H]1/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)O[C@@H]1C(C)C)O)/C.N1=CC=CC=C1>>CCCCC(=O)O.C(C1=CC=CC=C1)(=O)[O-].C[C@@H]1/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)O[C@@H]1C(C)C)O)/C | [CH3:1][C:2]1=[CH:3]\[C@@H:4]([OH:5])[CH2:6][C:7](=[O:8])[CH2:9][c:10]2[n:11][c:12]([cH:13][o:14]2)[C:15](=[O:16])[N:17]2[CH2:18][CH2:19][CH:20]=[C:21]2[C:22](=[O:23])[O:24][C@H:25]([CH:26]([CH3:27])[CH3:42])[C@H:29]([CH3:30])/[CH:31]=[CH:32]/[C:33](=[O:34])[NH:35][CH2:36]\[CH:37]=[CH:38]\1.Cl[C:43](Cl)=[O:45].n1[cH:51... | CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1.O=C(Cl)Cl.c1ccncc1 | CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1.CCCCC(=O)O.O=C([O-])c1ccccc1 | null | CN(C1=CC=NC=C1)C | CO | Acylation | OtherReaction | cfe35400cadfd3c4e212f419892cc43c93ab982f0361fecf852ae7d2e7039395 | f560654f091ced9bbfaef2c9014becc2de0bf0684d7a735cab18a32868d866d3 | O=C1CC/C=C/C=C/CNC(=O)/C=C/CCOC(=O)C2=CCCN2C(=O)c2coc(n2)C1.c1ccccc1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;H0;D1;+0:2].[C:3]=[C:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[CH;D3;+0:9](-[C;D1;H3:10])-[CH3;D1;+0:11])-[C:12]/[C:13]=[C:14].[c:15]1:[cH;D2;+0:16]:[c:17]:[cH;D2;+0:18]:n:[cH;D2;+0:19]:1>>[C:20]-[C:21]-[CH2;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:22])-[OH;D1;+0:2].[C:3]=[C:4]-[C:5](=[O;D1;H0:6])-[#8:7... | null | [] | null | null | null | null | The n-propionate, n-valerate, n-phenylacetate and benzoate derivatives of Virginiamycin M1 were prepared using the respective carbonyl chlorides. The respective carbonyl chloride (1.0 mmole) was added to a stirring solution of virginiamycin M1 (0.50 g, 0.95 mmole), pyridine (84 μl) and 4-dimethylaminopyridine (20 μg) a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide | Carboxylic acid | c1ccncc1 | c1ccccc1 | C1=C2COCC/C=C/CNC/C=C/C=C/CCCCc3nc(co3)CN2CC1.c1ccccc1 | null | CN(C1=CC=NC=C1)C.CO | null | null | CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1.O=C(Cl)Cl.c1ccncc1>CN(C1=CC=NC=C1)C.CO>CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1.CCCCC(=O)O.O=C([O-])c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-15280f38c7e244d1bfa07303e59094ac | ClCC1CO1.Clc1cccc(N2CCNCC2)c1>>Clc1cccc(N2CCN(CC3CO3)CC2)c1 | ClC=1C=C(C=CC1)N1CCNCC1.[H-].[Na+].C(Cl)C1CO1>>ClC=1C=C(C=CC1)N1CCN(CC1)CC1CO1 | Cl[CH2:11][CH:12]1[CH2:13][O:14]1.[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:15][CH2:16]2)[cH:17]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH:12]3[CH2:13][O:14]3)[CH2:15][CH2:16]2)[cH:17]1 | ClCC1CO1.Clc1cccc(N2CCNCC2)c1 | Clc1cccc(N2CCN(CC3CO3)CC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(N2CCN(CC3CO3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#7:5]1-[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2)-[C:9]-[C:10]-1 | null | [] | null | null | 30 | MINUTE | To a mixture of 1.50 g of 4-(3-chlorophenyl)-piperazine and 0.31 g of sodium hydride was added 2.4 ml of epichlorohydrin and the reaction mixture as stirred at room temperature for 30 minutes. After the reaction was completed, the reaction mixture was extracted with 100 ml of ethyl acetate, and the extract was washed 5... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1CO1 | HCl | null | null | 0.5 | ClCC1CO1.Clc1cccc(N2CCNCC2)c1>>Clc1cccc(N2CCN(CC3CO3)CC2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-42a64c7a9b4e47b98da6dccff107f5fc | Cc1cc(C)c(O)c(C(=O)Cc2ccccc2)c1>>C=C(C(=O)c1cc(C)cc(C)c1O)c1ccccc1 | CC1=CC(=C(C(=C1)C)O)C(CC1=CC=CC=C1)=O.C(C)(=O)OC(C)=O>>CC1=C(C(=CC(=C1)C)C(C(=C)C1=CC=CC=C1)=O)O | [CH2:2]([C:3](=[O:4])[c:5]1[cH:6][c:7]([CH3:8])[cH:9][c:10]([CH3:11])[c:12]1[OH:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH2:1]=[C:2]([C:3](=[O:4])[c:5]1[cH:6][c:7]([CH3:8])[cH:9][c:10]([CH3:11])[c:12]1[OH:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | Cc1cc(C)c(O)c(C(=O)Cc2ccccc2)c1 | C=C(C(=O)c1cc(C)cc(C)c1O)c1ccccc1 | null | null | CN(C)CN(C)C | Miscellaneous | OtherReaction | 8e727b298ec83d8c5d86a3a83dd18ad598c984927cb34414a5e2d1722bf0470d | a4ea716c40716a0b7f0a729baa69598349e4dc3a183004a01a28b0d16986acd9 | C=C(C(=O)c1ccccc1)c1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H2:8]=[C;H0;D3;+0:4](-[C:2](=[O;D1;H0:1])-[c:3])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 212.6 Grams of 4,6-dimethyl-2-(2-phenylacetyl)-phenol was dissolved in 350 ml of N,N,N',N'-tetramethyldiaminomethane, then under ice-cooled condition with stirring, 350 ml of acetic anhydride was added dropwise thereto. The reaction mixture was further stirred at room temperature for 2 hours, then was poured in 1 kg of... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone.Vinyl | null | null | c1ccccc1.c1ccccc1 | Other | CN(C)CN(C)C | null | null | Cc1cc(C)c(O)c(C(=O)Cc2ccccc2)c1>CN(C)CN(C)C>C=C(C(=O)c1cc(C)cc(C)c1O)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6ba3ad0efaef42adae43ee53ddb0b4a6 | C=C(C(=O)c1cc(C)cc(C)c1O)c1ccccc1>>Cc1cc(C)c2c(c1O)C(=O)C(c1ccccc1)C2 | S(O)(O)(=O)=O.CC1=C(C(=CC(=C1)C)C(C(=C)C1=CC=CC=C1)=O)O>>CC1=C2CC(C(C2=C(C(=C1)C)O)=O)C1=CC=CC=C1 | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([C:10](=[O:11])[C:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)=[CH2:19])[c:8]1[OH:9]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[C:10](=[O:11])[CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19]2 | C=C(C(=O)c1cc(C)cc(C)c1O)c1ccccc1 | Cc1cc(C)c2c(c1O)C(=O)C(c1ccccc1)C2 | null | null | null | C-C Coupling | OtherReaction | 4155d05fc05674edfa60b9265f47e228493dc10d1c115f74632cab156b34c6f4 | 2423fd262a32a267ed5d6ae9baff9668729a2c0a60281fcd676d6597312a598b | O=C1c2ccccc2CC1c1ccccc1 | [C;D1;H3:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5](-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH2;D1;+0:9])-[c:10](:[c:11]):[c:12]):[c:13]>>[C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[c:5](:[c:13])-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[c:10](:[c:11]):[c:12])-[CH2;D2;+0:9]-1 | 70.3 | [{"value": 70.3, "product": "CC1=C2CC(C(C2=C(C(=C1)C)O)=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into 15 ml of concentrated sulfuric acid, under ice-cooled condition with stirring, 3.0 g of 2,4-dimethyl-6-(2-phenylacryloyl)phenol was added gradually, then the whole mixture was stirred at room temperature for 1 hour. The reaction mixture was poured in 100 g of ice and extracted with 200 ml of methylene chloride. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Vinyl | Ketone | c1ccccc1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2.c1ccccc1 | null | null | null | null | C=C(C(=O)c1cc(C)cc(C)c1O)c1ccccc1>>Cc1cc(C)c2c(c1O)C(=O)C(c1ccccc1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-34bc9d0993fb467f9622700edbfc802b | CCC(=O)c1cc(C)ccc1OC.O=Cc1ccccc1>>COc1ccc(C)cc1C(=O)C(C)=Cc1ccccc1 | Cl.COC1=C(C=C(C=C1)C)C(CC)=O.C(C1=CC=CC=C1)=O.[OH-].[Na+]>>COC1=C(C=C(C=C1)C)C(C(C)=CC1=CC=CC=C1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1[C:10](=[O:11])[CH2:12][CH3:13].O=[CH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1[C:10](=[O:11])[C:12]([CH3:13])=[CH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | CCC(=O)c1cc(C)ccc1OC.O=Cc1ccccc1 | COc1ccc(C)cc1C(=O)C(C)=Cc1ccccc1 | null | null | C(C)O | C-C Coupling | Aldol condensation | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(C=Cc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[C;D1;H3:5]-[C;H0;D3;+0:6](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:7](=[O;D1;H0:8])-[c:9] | 101.3 | [{"value": 101.3, "product": "COC1=C(C=C(C=C1)C)C(C(C)=CC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 140 g of 2'-methoxy-5'-methylpropiophenone, 83.4 g of benzaldehyde and 1.5 liters of ethanol was added 154 ml of 20%-sodium hydroxide aqueous solution under stirring. The reaction mixture was stirred overnight at room temperature, then 10%-hydrochloric acid was added to make the reaction mixture acidic,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)O | null | null | CCC(=O)c1cc(C)ccc1OC.O=Cc1ccccc1>C(C)O>COc1ccc(C)cc1C(=O)C(C)=Cc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-052823d5aace48c1ba767bdcf24f3608 | CC=CCBr.Cc1ccc(O)c2c1C(c1ccccc1)C(C)C2=O>>CC=CCOc1ccc(C)c2c1C(=O)C(C)C2c1ccccc1 | CC1C(C2=C(C=CC(=C2C1C1=CC=CC=C1)C)O)=O.C(C=CC)Br.[OH-].[K+]>>CC1C(C2=C(C=CC(=C2C1C1=CC=CC=C1)C)OCC=CC)=O | Br[CH2:4][CH:3]=[CH:2][CH3:1].[OH:5][c:6]1[cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[C:13](=[O:14])[CH:15]([CH3:16])[CH:17]2[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH:2]=[CH:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[C:13](=[O:14])[CH:15]([CH3:16])[CH:17]2[c:18]1[cH:19][cH:20][cH:21][cH:2... | CC=CCBr.Cc1ccc(O)c2c1C(c1ccccc1)C(C)C2=O | CC=CCOc1ccc(C)c2c1C(=O)C(C)C2c1ccccc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1CC(c2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]=[C:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[C;D1;H3:4]-[C:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:6]=[O;D1;H0:5] | null | [] | null | null | null | null | A solution of 19.0 g of 2,3-dihydro-2,4-dimethyl-3-phenyl-7-hydroxy-1H-inden-1-one, 13.98 of crotyl bromide and 5.47 g of potassium hydroxide in 200 ml of acetone was heated and refluxed under stirring condition. After the reaction was completed, the reaction mixture was concentrated and extracted with ethyl acetate, t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCC2.c1ccccc1 | HBr | CC(=O)C | null | null | CC=CCBr.Cc1ccc(O)c2c1C(c1ccccc1)C(C)C2=O>CC(=O)C>CC=CCOc1ccc(C)c2c1C(=O)C(C)C2c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6c48a288eea14ea8baf5587a401e78ea | CC=CCOC1=C2C(=O)C(C)C(c3ccccc3)C2C(C)(C)C=C1>>C=CC(C)c1cc(C)c2c(c1O)C(=O)C(C)C2c1ccccc1 | CC1C(C2=C(C=CC(C2C1C1=CC=CC=C1)(C)C)OCC=CC)=O.C1CCCC2=CC=CC=C12>>CC1C(C2=C(C(=CC(=C2C1C1=CC=CC=C1)C)C(C=C)C)O)=O | C[CH:1]=[CH:2][CH2:3][O:12][C:11]1=[C:10]2[CH:9]([C:7]([CH3:4])([CH3:8])[CH:6]=[CH:5]1)[CH:17]([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH:15]([CH3:16])[C:13]2=[O:14]>>[CH2:1]=[CH:2][CH:3]([CH3:4])[c:5]1[cH:6][c:7]([CH3:8])[c:9]2[c:10]([c:11]1[OH:12])[C:13](=[O:14])[CH:15]([CH3:16])[CH:17]2[c:18]1[cH:19][cH:20][cH:... | CC=CCOC1=C2C(=O)C(C)C(c3ccccc3)C2C(C)(C)C=C1 | C=CC(C)c1cc(C)c2c(c1O)C(=O)C(C)C2c1ccccc1 | null | null | null | Reduction | OtherReaction | 13e7d01d96a7a39dd17690ed95846f10d5e8bce3f12253414108fa34b1aaca16 | 16754b677ebdcf46afa3a9c8052379e86abe479ed7daf3a89b8d84ac07715eb0 | O=C1CC(c2ccccc2)c2ccccc21 | C-[CH;D2;+0:1]=[C:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[C;H0;D3;+0:5]1=[C;H0;D3;+0:6]2-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[c:11])-[CH;D3;+0:12]-2-[C;H0;D4;+0:13](-[C;D1;H3:14])(-[CH3;D1;+0:15])-[CH;D2;+0:16]=[CH;D2;+0:17]-1>>[C;D1;H3:14]-[c;H0;D3;+0:13]1:[cH;D2;+0:16]:[c;H0;D3;+0:17](-[CH;D3;+0:3](-[CH3;D1;+0:15])-[C:2]=[CH2... | null | [] | null | null | null | null | 11 Grams of 2,3-dihydro-2,4-dimethyl-3-phenyl-4-methyl-7-crotyloxy-1H-inden-1-one was added to 55 ml of tetrahydronaphthalene and the mixture was heated and refluxed for 6 hours with stirring condition. After the reaction was completed, the reaction mixture was concentrated by removal of the solvent, and the residue th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Ketone.Aromatic alcohol.Vinyl | C1=CCC2CCCC2=C1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2.c1ccccc1 | Other | null | null | null | CC=CCOC1=C2C(=O)C(C)C(c3ccccc3)C2C(C)(C)C=C1>>C=CC(C)c1cc(C)c2c(c1O)C(=O)C(C)C2c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6737505c6dd04f6cbd916f255e400141 | COc1ccc(C=O)cc1.Cc1cc(C)c2c(c1O)C(=O)CC2>>COc1ccc(C=C2Cc3c(C)cc(C)c(O)c3C2=O)cc1 | CC1=C2CCC(C2=C(C(=C1)C)O)=O.[H-].[Na+].Cl.C(C1=CC=C(C=C1)OC)=O>>CC1=C2CC(C(C2=C(C(=C1)C)O)=O)=CC1=CC=C(C=C1)OC | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][cH:21]1.[CH2:8]1[CH2:9][c:10]2[c:11]([CH3:12])[cH:13][c:14]([CH3:15])[c:16]([OH:17])[c:18]2[C:19]1=[O:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[C:8]2[CH2:9][c:10]3[c:11]([CH3:12])[cH:13][c:14]([CH3:15])[c:16]([OH:17])[c:18]3[C:19]2=[O:20])[cH:21][cH:22]1 | COc1ccc(C=O)cc1.Cc1cc(C)c2c(c1O)C(=O)CC2 | COc1ccc(C=C2Cc3c(C)cc(C)c(O)c3C2=O)cc1 | null | null | CN(C=O)C | C-C Coupling | Aldol condensation | 68e28f9095e1f150f32da6921211b9a27c818a0dd75d077bb5baa7c9b256c798 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C1C(=Cc2ccccc2)Cc2ccccc21 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[O;D1;H0:5]=[C:6]1-[c:10]:[c:9]-[C:8]-[C;H0;D3;+0:7]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | 10 Grams of 2,3-dihydro-4,6dimethyl-7-hydroxy-1H-inden-1-one was dissolved in 200 ml of dimethylformamide, then 5.45 g of 60%-sodium hydride was added gradually thereto and the reaction mixture was stirred at room temperature for 30 minutes. Next, 6.91 ml of p-anisaldehyde was added to the reaction mixture and further ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccccc1.c1ccc2c(c1)CCC2 | HO- | CN(C=O)C | null | 0.5 | COc1ccc(C=O)cc1.Cc1cc(C)c2c(c1O)C(=O)CC2>CN(C=O)C>COc1ccc(C=C2Cc3c(C)cc(C)c(O)c3C2=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d57a0be166b945c9b5bbf688d179b281 | COc1ccc(C=C2Cc3c(C)cc(C)c(O)c3C2=O)cc1>>COc1ccc(CC2Cc3c(C)cc(C)c(O)c3C2=O)cc1 | CC1=C2CC(C(C2=C(C(=C1)C)O)=O)=CC1=CC=C(C=C1)OC.[H][H]>>CC1=C2CC(C(C2=C(C(=C1)C)O)=O)CC1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[C:8]2[CH2:9][c:10]3[c:11]([CH3:12])[cH:13][c:14]([CH3:15])[c:16]([OH:17])[c:18]3[C:19]2=[O:20])[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH:8]2[CH2:9][c:10]3[c:11]([CH3:12])[cH:13][c:14]([CH3:15])[c:16]([OH:17])[c:18]3[C:19]2=[O:20])[cH:21][cH:22]1 | COc1ccc(C=C2Cc3c(C)cc(C)c(O)c3C2=O)cc1 | COc1ccc(CC2Cc3c(C)cc(C)c(O)c3C2=O)cc1 | null | [Pd] | C(C)(=O)O.C(C)OC(C)=O | Reduction | Hydrogenation (double to single) | 5fe69a962c1ddcaf237655de8a7bd4295358470be9169bf50f1a13abc64ccb24 | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | O=C1c2ccccc2CC1Cc1ccccc1 | [O;D1;H0:1]=[C:2]1-[c:3]:[c:4]-[C:5]-[C;H0;D3;+0:6]-1=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:1]=[C:2]1-[c:3]:[c:4]-[C:5]-[CH;D3;+0:6]-1-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | 16.09 Grams of 2,3-dihydro-4,6-dimethyl-7-hydroxy-2-(4-methoxybenzylidene)-1H-inden-1-one was dissolved in a mixed solvent of 150 ml of ethylacetate with 100 ml of acetic acid, this solution was let subjected to catalytic reduction at room temperature under 3 atmospheric hydrogen gas pressure in the presence of 1.5 g o... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccccc1.c1ccc2c(c1)CCC2 | null | [Pd].C(C)(=O)O.C(C)OC(C)=O | null | null | COc1ccc(C=C2Cc3c(C)cc(C)c(O)c3C2=O)cc1>[Pd].C(C)(=O)O.C(C)OC(C)=O>COc1ccc(CC2Cc3c(C)cc(C)c(O)c3C2=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8f9739c2897a4ca38d26a99bddb1c9c6 | CI.CI.Cc1cc(C)c2c(c1O)C(=O)C(Cc1ccccc1)C2>>COc1c(C)cc(C)c2c1C(=O)C(C)(Cc1ccccc1)C2 | CI.CI.[H-].[Na+].[H-].[Na+].CI.[H-].[Na+].CC1=C2CC(C(C2=C(C(=C1)C)O)=O)CC1=CC=CC=C1.CN(C=O)C>>CC1(C(C2=C(C(=CC(=C2C1)C)C)OC)=O)CC1=CC=CC=C1 | I[CH3:14].I[CH3:1].[OH:2][c:3]1[c:4]([CH3:5])[cH:6][c:7]([CH3:8])[c:9]2[c:10]1[C:11](=[O:12])[CH:13]([CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[CH2:22]2>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[cH:6][c:7]([CH3:8])[c:9]2[c:10]1[C:11](=[O:12])[C:13]([CH3:14])([CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[CH2:22... | CI.CI.Cc1cc(C)c2c(c1O)C(=O)C(Cc1ccccc1)C2 | COc1c(C)cc(C)c2c1C(=O)C(C)(Cc1ccccc1)C2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b65b8ab67b29032cf7e72f98925bdecd023b43c5fd0cc86b78a2734e0244d18f | d3b40c25cee517c44ea4ad61b807727049a1dbe3a5da7e0bdf8fa8a979b54712 | O=C1c2ccccc2CC1Cc1ccccc1 | I-[CH3;D1;+0:1].I-[CH3;D1;+0:2].[O;D1;H0:3]=[C:4]1-[CH;D3;+0:5](-[C:6]-[c:7])-[C:8]-[c:9]:[c:10]-1:[c:11](-[OH;D1;+0:12]):[c:13]>>[CH3;D1;+0:1]-[C;H0;D4;+0:5]1(-[C:6]-[c:7])-[C:8]-[c:9]:[c:10](:[c:11](-[O;H0;D2;+0:12]-[CH3;D1;+0:2]):[c:13])-[C:4]-1=[O;D1;H0:3] | null | [] | null | null | 40 | MINUTE | 28.3 Grams of 2,3-dihydro-4,6-dimethyl-7-hydroxy-2-benzyl-1H-inden-1-one was dissolved in 350 ml of dimethylformamide, then 5.2 g of 60%-sodium hydride was added thereto at 55°-60° C. and the mixture was stirred for 40 minutes. Next 8 ml of methyl iodide was added thereto, and the whole mixture was heated to the same t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic alcohol | Ketone.Ether | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2.c1ccccc1 | HI | null | null | 0.666667 | CI.CI.Cc1cc(C)c2c(c1O)C(=O)C(Cc1ccccc1)C2>>COc1c(C)cc(C)c2c1C(=O)C(C)(Cc1ccccc1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-adac67716cd442838e451fe27a615b95 | COc1c(C)cc(C)c2c1C(=O)C(C)(Cc1ccccc1)C2>>Cc1cc(C)c2c(c1O)C(=O)C(C)(Cc1ccccc1)C2 | CC1(C(C2=C(C(=CC(=C2C1)C)C)OC)=O)CC1=CC=CC=C1.[I-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-]>>CC1(C(C2=C(C(=CC(=C2C1)C)C)O)=O)CC1=CC=CC=C1 | C[O:9][c:8]1[c:2]([CH3:1])[cH:3][c:4]([CH3:5])[c:6]2[c:7]1[C:10](=[O:11])[C:12]([CH3:13])([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21]2>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[C:10](=[O:11])[C:12]([CH3:13])([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21]2 | COc1c(C)cc(C)c2c1C(=O)C(C)(Cc1ccccc1)C2 | Cc1cc(C)c2c(c1O)C(=O)C(C)(Cc1ccccc1)C2 | null | null | C(C)#N | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1c2ccccc2CC1Cc1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6]>>[O;D1;H0:6]=[C:5]-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | 1 | HOUR | 23.0 Grams of 2,3-dihydro-2,4,6-trimethyl-7-methoxy-2-benzyl-1H-inden-1-one and 25.8 g of sodium iodide were dissolved in 90 ml of acetonitrile. To this solution was added 22.9 g of aluminium chloride at room temperature and stirred for 1 hour. Then the solvent was removed by evaporation under a reduced pressure, and t... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CCC2.c1ccccc1 | Other | C(C)#N | null | 1 | COc1c(C)cc(C)c2c1C(=O)C(C)(Cc1ccccc1)C2>C(C)#N>Cc1cc(C)c2c(c1O)C(=O)C(C)(Cc1ccccc1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-502e59e83d8340a4bd3c79ffc19efc01 | Cc1cc(C)c2c(c1O)C(=O)C(c1ccccc1)C2.NCc1ccccc1>>Cc1cc(C)c2c(c1O)C(NCc1ccccc1)=C(c1ccccc1)C2 | C(C1=CC=CC=C1)N.CC1=C2CC(C(C2=C(C(=C1)C)O)=O)C1=CC=CC=C1>>CC1=C2CC(=C(C2=C(C(=C1)C)O)NCC1=CC=CC=C1)C1=CC=CC=C1 | O=[C:10]1[c:7]2[c:6]([c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:8]2[OH:9])[CH2:26][CH:19]1[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[NH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[C:10]([NH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[C:19]... | Cc1cc(C)c2c(c1O)C(=O)C(c1ccccc1)C2.NCc1ccccc1 | Cc1cc(C)c2c(c1O)C(NCc1ccccc1)=C(c1ccccc1)C2 | null | null | ClCCl.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 0225b4cf4172c35cf0f5dd47b9f096e409bbf086547d0dcddb2e11950b6f8a4c | 9b18df0b1b6fcaae08dc7ad79d6e80286547463fea1b02a7014d39df0face74d | c1ccc(CNC2=C(c3ccccc3)Cc3ccccc32)cc1 | O=[C;H0;D3;+0:1]1-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[C:6]-[c:7]:[c:8]-1:[c:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[c:12]-[C:11]-[NH;D2;+0:10]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[C:6]-[c:7]:[c:8]-1:[c:9] | null | [] | null | null | 2 | DAY | 5.0 Grams of 4,6-dimethyl-7-hydroxy-2-phenyl-1-indanone was dissolved in 10 ml of diethyl ether and 10 ml of dichloromethane, then this solution was added dropwise gradually to a mixture of a solution of 2.55 ml of benzylamine in 10 ml of diethyl ether with 8 g of Molecular sieves 5A. The whole mixture was stirred at r... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Enamine | c1ccc2c(c1)CCC2 | C1=Cc2ccccc2C1 | c1ccccc1.c1ccccc1.C1=Cc2ccccc2C1 | HO- | ClCCl.C(C)OCC | null | 48 | Cc1cc(C)c2c(c1O)C(=O)C(c1ccccc1)C2.NCc1ccccc1>ClCCl.C(C)OCC>Cc1cc(C)c2c(c1O)C(NCc1ccccc1)=C(c1ccccc1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8a19649ebcff469e91efc72f600ed2a4 | C=CC(c1ccccc1)c1cc(C)c2c(c1O)C(=O)CC2.NO>>C=CC(c1ccccc1)c1cc(C)c2c(c1O)C(=NO)CC2 | OC=1C(=CC(=C2CCC(C12)=O)C)C(C=C)C1=CC=CC=C1.Cl.NO.N1=CC=CC=C1>>OC=1C(=CC(=C2CCC(C12)=NO)C)C(C=C)C1=CC=CC=C1 | O=[C:18]1[c:15]2[c:14]([c:12]([CH3:13])[cH:11][c:10]([CH:3]([CH:2]=[CH2:1])[c:4]3[cH:5][cH:6][cH:7][cH:8][cH:9]3)[c:16]2[OH:17])[CH2:22][CH2:21]1.[NH2:19][OH:20]>>[CH2:1]=[CH:2][CH:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][c:12]([CH3:13])[c:14]2[c:15]([c:16]1[OH:17])[C:18](=[N:19][OH:20])[CH2:21][CH2:22]2 | C=CC(c1ccccc1)c1cc(C)c2c(c1O)C(=O)CC2.NO | C=CC(c1ccccc1)c1cc(C)c2c(c1O)C(=NO)CC2 | null | null | C(C)O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | d568a813624bc83ce2d54e68541f55806c5d1b8d76589e5db8b5244a53b556d2 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C1CCc2ccc(Cc3ccccc3)cc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[c:4]:[c:5]-1:[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[O;D1;H1:8]-[N;H0;D2;+0:7]=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[c:4]:[c:5]-1:[c:6] | null | [] | null | null | null | null | An ethanol solution containing 120 g of 2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one, 45 of hydroxylamine hydrochloride and 200 ml of pyridine in 1,200 ml of ethanol was refluxed for 4 hours. After the reaction was completed, the reaction mixture was concentrated to dryness under a reduced pres... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccccc1.c1ccc2c(c1)CCC2 | HO- | C(C)O.C(C)(=O)OCC | null | null | C=CC(c1ccccc1)c1cc(C)c2c(c1O)C(=O)CC2.NO>C(C)O.C(C)(=O)OCC>C=CC(c1ccccc1)c1cc(C)c2c(c1O)C(=NO)CC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-484afa8140964d98ab10e3c32c381780 | Cc1cc(C)c2c(c1O)C(=NO)C(c1ccccc1)C2>>Cc1cc(C)c2c(c1O)C(N)C(c1ccccc1)C2 | [H][H].CC1=C2CC(C(C2=C(C(=C1)C)O)=NO)C1=CC=CC=C1.C([O-])(O)=O.[Na+]>>NC1C(CC2=C(C=C(C(=C12)O)C)C)C1=CC=CC=C1 | O[N:11]=[C:10]1[c:7]2[c:6]([c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:8]2[OH:9])[CH2:19][CH:12]1[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[CH:10]([NH2:11])[CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19]2 | Cc1cc(C)c2c(c1O)C(=NO)C(c1ccccc1)C2 | Cc1cc(C)c2c(c1O)C(N)C(c1ccccc1)C2 | null | [Pt]=O | C(C)(=O)O.O | Reduction | OtherReaction | 08ed11e7765d720087e6db4e55e2b90e6f8f791930986709debdb3fe2981255e | 4a7bf747f64425b21ceaa04fbc4c046ccf522c774aa5649ec92eba03e46bfee5 | c1ccc(C2Cc3ccccc3C2)cc1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2]1-[C:3](-[c:4])-[C:5]-[c:6]:[c:7]-1:[c:8]>>[NH2;D1;+0:1]-[CH;D3;+0:2]1-[C:3](-[c:4])-[C:5]-[c:6]:[c:7]-1:[c:8] | null | [] | null | null | null | null | 3.00 Grams of 2,3-dihydro-4,6-dimethyl-7-hydroxy-2-phenyl-1H-inden-1-one oxime was dissolved in 55 ml of glacial acetic acid, and this solution was subjected to catalytic hydrogenation in the presence of 0.3 g of platinum oxide at room temperature under 4 atmospheric hydrogen gas pressure. The hydrogenation was termina... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Primary amine | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2.c1ccccc1 | Other | [Pt]=O.C(C)(=O)O.O | null | null | Cc1cc(C)c2c(c1O)C(=NO)C(c1ccccc1)C2>[Pt]=O.C(C)(=O)O.O>Cc1cc(C)c2c(c1O)C(N)C(c1ccccc1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7a603da7931848aeaaadbcc3c883c330 | Cc1cc(CNC(=O)CCl)c(O)c2c1CCC2=O.Cl.NO.c1ccncc1>>CNC(=O)C[n+]1ccccc1-c1cc(C)c2c(c1O)C(=NO)CC2.[Cl-] | ClCC(=O)NCC1=CC(=C2CCC(C2=C1O)=O)C.Cl.NO.N1=CC=CC=C1.C(C)O.O>>[Cl-].OC=1C(=CC(=C2CCC(C12)=NO)C)C1=[N+](C=CC=C1)CC(=O)NC | O=[C:20]1[c:17]2[c:16]([c:14]([CH3:15])[cH:13][c:12]([CH2:1][NH:2][C:3](=[O:4])[CH2:5]Cl)[c:18]2[OH:19])[CH2:24][CH2:23]1.[ClH:25].[NH2:21][OH:22].[n:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][n+:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1-[c:12]1[cH:13][c:14]([CH3:15])[c:16]2[c:17]([c:18]1[OH:19])... | Cc1cc(CNC(=O)CCl)c(O)c2c1CCC2=O.Cl.NO.c1ccncc1 | CNC(=O)C[n+]1ccccc1-c1cc(C)c2c(c1O)C(=NO)CC2.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | da2ebec24ad4bda4eb44b89b53829611c74d3ac2f9a7a98ba79659351b2611c0 | a925866e583992e6229d06e4479581de732bc0f8c7b97e6ace224de2a5069c6f | N=C1CCc2ccc(-c3cccc[nH+]3)cc21 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[CH2;D2;+0:5]-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]2:[c:10](:[c:11]:1-[O;D1;H1:12])-[C;H0;D3;+0:13](=O)-[C:14]-[C:15]-2.[ClH;D0;+0:16].[NH2;D1;+0:17]-[O;D1;H1:18].[c:19]1:[c:20]:[c:21]:[c:22]:[n;H0;D2;+0:23]:[cH;D2;+0:24]:1>>[CH3;D1;+0:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-... | null | [] | null | null | null | null | 200 Grams of 6-chloroacetylaminomethyl-2,3-dihydro-7-hydroxy-4-methyl-1H-indene-1-one, 77.9 g of hydroxylamine hydrochloride, 300 ml of pyridine and 1,800 ml of ethanol were refluxed for 3 hours. After the reaction was completed, the solvent was removed by evaporation under a reduced pressure, then to the residue thus ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | Oxime | c1ccc2c(c1)CCC2.c1ccncc1 | C1=CC=[NH+]C=C1.c1ccc2c(c1)CCC2 | C1=CC=[NH+]C=C1.c1ccc2c(c1)CCC2 | HCl | null | null | null | Cc1cc(CNC(=O)CCl)c(O)c2c1CCC2=O.Cl.NO.c1ccncc1>>CNC(=O)C[n+]1ccccc1-c1cc(C)c2c(c1O)C(=NO)CC2.[Cl-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d663bb38b73a4b6a95407d3d1f310bd1 | Cc1cc(C)c2c(c1O)C(N)C(C)(C)C2.Clc1cccc(N2CCN(CC3CO3)CC2)c1>>Cc1cc(C)c2c(c1O)C(NCC(O)CN1CCN(c3cccc(Cl)c3)CC1)C(C)(C)C2 | ClC=1C=C(C=CC1)N1CCN(CC1)CC1CO1.Cl.NC1C(CC2=C(C=C(C(=C12)O)C)C)(C)C.C([O-])(O)=O.[Na+]>>ClC=1C=C(C=CC1)N1CCN(CC1)CC(CNC1C(CC2=C(C=C(C(=C12)O)C)C)(C)C)O | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[CH:10]([NH2:11])[C:29]([CH3:30])([CH3:31])[CH2:32]2.[CH2:12]1[CH:13]([CH2:15][N:16]2[CH2:17][CH2:18][N:19]([c:20]3[cH:21][cH:22][cH:23][c:24]([Cl:25])[cH:26]3)[CH2:27][CH2:28]2)[O:14]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[CH:10]([NH:11][C... | Cc1cc(C)c2c(c1O)C(N)C(C)(C)C2.Clc1cccc(N2CCN(CC3CO3)CC2)c1 | Cc1cc(C)c2c(c1O)C(NCC(O)CN1CCN(c3cccc(Cl)c3)CC1)C(C)(C)C2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc(N2CCN(CCCNC3CCc4ccccc43)CC2)cc1 | [C:1]-[C:2](-[NH2;D1;+0:3])-[c:4].[C:5]-[C:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1>>[C:5]-[C:6](-[OH;D1;+0:8])-[CH2;D2;+0:7]-[NH;D2;+0:3]-[C:2](-[C:1])-[c:4] | null | [] | null | null | null | null | 0.21 Gram of 4-(3-chlorophenyl)-1-(2,3-epoxypropyl)piperazine was added to a solution containing 0.21 g of 1-amino-2,3-dihydro-7-hyroxy-2,2,4,6-tetramethyl-1H-indene hydrochloride in 10 ml of ethanol solution, and the mixture was refluxed for 5 hours. After the reaction was completed, the reaction mixture was concentra... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCC2 | null | C(C)O | null | null | Cc1cc(C)c2c(c1O)C(N)C(C)(C)C2.Clc1cccc(N2CCN(CC3CO3)CC2)c1>C(C)O>Cc1cc(C)c2c(c1O)C(NCC(O)CN1CCN(c3cccc(Cl)c3)CC1)C(C)(C)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-078c67ca02f34b0ebcf180a005a5ee53 | CC(C)(C)c1ccc(O)cc1.O=C(O)CCl>>CC(C)(C)c1ccc(OCC(=O)O)cc1 | Cl.[O-]C1=CC=CC=C1.ClCC(=O)O.C(C)(C)(C)C1=CC=C(C=C1)O.[H-].[Na+]>>C(C)(C)(C)C1=CC=C(OCC(=O)O)C=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:14][cH:15]1.Cl[CH2:10][C:11](=[O:12])[OH:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][cH:15]1 | CC(C)(C)c1ccc(O)cc1.O=C(O)CCl | CC(C)(C)c1ccc(OCC(=O)O)cc1 | null | null | CN(C=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[O;D1;H1:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 2 | HOUR | A solution of 10.0 g (66.7 mmoles) p-tertbutylphenol in 50 ml dry dimethyl formamide was added, dropwise, to a mechanically stirred slurry of 8.4 g sodium hydride (as 50% oil dispersion) in 500 ml dry dimethyl formamide. To the phenoxide solution was added, dropwise, a solution of 6.3 g (66.3 mmoles) chloroacetic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | CN(C=O)C.C(C)OCC | null | 2 | CC(C)(C)c1ccc(O)cc1.O=C(O)CCl>CN(C=O)C.C(C)OCC>CC(C)(C)c1ccc(OCC(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a60661e61dbd460e97c33f1dc796e5e7 | C=CC(=O)OCCCC.CC(C)(C)c1ccc(O)cc1>>CCCCOC(=O)CCOc1ccc(C(C)(C)C)cc1 | C(C)(C)(C)C1=CC=C(C=C1)O.[H-].[Na+].C(C=C)(=O)OCCCC>>C(C)(C)(C)C1=CC=C(OCCC(=O)OCCCC)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[CH:8]=[CH2:9].[OH:10][c:11]1[cH:12][cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]1 | C=CC(=O)OCCCC.CC(C)(C)c1ccc(O)cc1 | CCCCOC(=O)CCOc1ccc(C(C)(C)C)cc1 | null | C1(=CC=CC=C1)NC1=CC2=CC=CC=C2C=C1 | null | Heteroatom Alkylation and Arylation | oxa-Michael addition | b8096e54ed86799f66881af349819a909cf96ddbe65e72778397bf9f04362595 | cae213716dcbbf15dfd02ec8131fb87168e0289c8ec38df35ccae1ab4bb8b4b2 | c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 45.2 | [{"value": 45.0, "product": "C(C)(C)(C)C1=CC=C(OCCC(=O)OCCCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.2, "product": "C(C)(C)(C)C1=CC=C(OCCC(=O)OCCCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 25 g (0.167 mole) p-tert-butylphenol, 0.2 g sodium hydride (as 50% dispersion in oil), 0.2 g N-phenyl-2-naphthylamine (as basic polymerization inhibitor) in 75.0 g (0.586 mole) butyl acrylate was heated at 125° C. for four hours. The temperature was then reduced to 100° C. and the excess acrylate distille... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic alcohol.Vinyl | Ester.Ether | null | null | c1ccccc1 | null | C1(=CC=CC=C1)NC1=CC2=CC=CC=C2C=C1 | null | null | C=CC(=O)OCCCC.CC(C)(C)c1ccc(O)cc1>C1(=CC=CC=C1)NC1=CC2=CC=CC=C2C=C1>CCCCOC(=O)CCOc1ccc(C(C)(C)C)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5c7452413c6c4954b4611120e361a41f | CCCCOC(=O)CCOc1ccc(C(C)(C)C)cc1>>CC(C)(C)c1ccc(OCCCO)cc1 | C(C)(C)(C)C1=CC=C(OCCC(=O)OCCCC)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)(C)(C)C1=CC=C(OCCCO)C=C1 | CCCCO[C:12]([CH2:11][CH2:10][O:9][c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:15][cH:14]1)=[O:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][OH:13])[cH:14][cH:15]1 | CCCCOC(=O)CCOc1ccc(C(C)(C)C)cc1 | CC(C)(C)c1ccc(OCCCO)cc1 | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C-C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | -5 | CELSIUS | null | null | This ester 21.0 g was dissolved in 500 ml dry ether and cooled to -5° C. in an ice/acetone bath. To the cold solution was added, cautiously, a slurry of 3.5 g lithium aluminum hydride in 100 ml dry ether. After one hour the excess lithium aluminum hydride was destroyed by the cautious addition of 200 ml ethyl acetate, ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | CCOCC | -5 | null | CCCCOC(=O)CCOc1ccc(C(C)(C)C)cc1>CCOCC>CC(C)(C)c1ccc(OCCCO)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cebef95bc8384043b4a84d71a6aab475 | CC(=O)OCCCCCl.CC(C)(C)c1ccc(O)cc1>>CC(=O)OCCCCOc1ccc(C(C)(C)C)cc1 | C(C)(C)(C)C1=CC=C(C=C1)O.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.C(C)(=O)OCCCCCl.[H-].[Na+]>>C(C)(=O)OCCCCOC1=CC=C(C=C1)C(C)(C)C | Cl[CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3].[OH:9][c:10]1[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19]1 | CC(=O)OCCCCCl.CC(C)(C)c1ccc(O)cc1 | CC(=O)OCCCCOc1ccc(C(C)(C)C)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | To a stirred slurry of 1.6 g sodium hydride (as 50% dispersion in oil) in 50 ml dry dimethyl formamide was added, drop-wise, a solution of 5.0 g p-tert-butylphenol (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution stirred under nitrogen until the phenoxide had totally formed. To the phenoxide was added a s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | CN(C=O)C | null | null | CC(=O)OCCCCCl.CC(C)(C)c1ccc(O)cc1>CN(C=O)C>CC(=O)OCCCCOc1ccc(C(C)(C)C)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-738ff1beafd14a068396998334793f43 | C=CCCCOc1ccc(C(C)(C)C)cc1.OO>>CC(C)(C)c1ccc(OCCCCCO)cc1 | OO.C(C)(C)(C)C1=CC=C(OCCCC=C)C=C1.C1(CCCCCCCB1)C1CCCCCCCC1.[OH-].[Na+]>>C(C)(C)(C)C1=CC=C(OCCCCCO)C=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14])[cH:16][cH:17]1.O[OH:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[cH:16][cH:17]1 | C=CCCCOc1ccc(C(C)(C)C)cc1.OO | CC(C)(C)c1ccc(OCCCCCO)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | a60d6b71e8ccffcb99d0520269e8a26dfb6e6127271b139d41fb1b3b13102989 | 1ce8c00754fe0f5a8ed975b07fdc26de74ee4b991b12a7a47b4cd82546d5f701 | c1ccccc1 | O-[OH;D1;+0:1].[C:2]-[C:3]-[CH;D2;+0:4]=[CH2;D1;+0:5]>>[C:2]-[C:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[OH;D1;+0:1] | null | [] | null | null | null | null | The 5-(p-tert-butylphenoxy)-1-pentene (10.5 g) was treated with 115 ml 0.5M 9-borabicyclononane in tetrahydrofuran and the reaction mixture was stirred at reflux for one hour. The solution was cooled to room temperature and treated with 25 ml 3N sodium hydroxide, then 10 ml 30% hydrogen peroxide. After the bubbling cea... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Allyl | Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1 | null | null | C=CCCCOc1ccc(C(C)(C)C)cc1.OO>O1CCCC1>CC(C)(C)c1ccc(OCCCCCO)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f4c51992232e47eea151c3071a97aad7 | COC(=O)CCCCCCCCCCOc1ccc(C(C)(C)C)cc1>>CC(C)(C)c1ccc(OCCCCCCCCCCCO)cc1 | C(C)(C)(C)C1=CC=C(OCCCCCCCCCCC(=O)OC)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)(C)(C)C1=CC=C(OCCCCCCCCCCCO)C=C1 | CO[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:9][c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:23][cH:22]1)=[O:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20... | COC(=O)CCCCCCCCCCOc1ccc(C(C)(C)C)cc1 | CC(C)(C)c1ccc(OCCCCCCCCCCCO)cc1 | null | null | C(C)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | The methyl 11-(p-tert-butylphenoxy)-undecanoate, 3.7 g, 10.6 mmoles, was dissolved in 100 ml dry diethyl ether and added, dropwise, to a stirred slurry of 0.5 g lithium aluminum hydride in 100 ml dry diethyl ether. After one hour the reaction mixture was filtered through Celite and the filtrate was treated with 100 ml ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C(C)OCC | null | null | COC(=O)CCCCCCCCCCOc1ccc(C(C)(C)C)cc1>C(C)OCC>CC(C)(C)c1ccc(OCCCCCCCCCCCO)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d238f04b14bc48fe99e1c99449a0250c | O=C(O)c1cccnc1.O=S(Cl)Cl>>O=C(Cl)c1cccnc1 | C(C)(C)(C)C1=CC=C(OCCCCO)C=C1.C(C1=CN=CC=C1)(=O)O.S(=O)(Cl)Cl>>C(C1=CN=CC=C1)(=O)Cl | O[C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1 | O=C(O)c1cccnc1.O=S(Cl)Cl | O=C(Cl)c1cccnc1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccncc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8] | 45 | [{"value": 45.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Nicotinoyl chloride was prepared by treating 100 g (0.81 mole) of nicotinic acid with 280 ml of thionyl chloride at reflux for two hours. The excess thionyl chloride was removed in vacuo and the crystalline acid chloride hydrochloride was suspended in 500 ml of dichloromethane. To the stirred mixture was added 66 g (0.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccncc1 | HCl | ClCCl | null | null | O=C(O)c1cccnc1.O=S(Cl)Cl>ClCCl>O=C(Cl)c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b90695a4db264d22bbc68b312dd6ff62 | O=C(O)C(O)CCl.Oc1ccc(Cl)cc1>>O=C(O)C(O)COc1ccc(Cl)cc1 | ClCC(C(=O)O)O.ClC1=CC=C(C=C1)O.Cl>>ClC1=CC=C(OCC(C(=O)O)O)C=C1 | Cl[CH2:6][CH:4]([C:2](=[O:1])[OH:3])[OH:5].[OH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[O:1]=[C:2]([OH:3])[CH:4]([OH:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | O=C(O)C(O)CCl.Oc1ccc(Cl)cc1 | O=C(O)C(O)COc1ccc(Cl)cc1 | null | null | [OH-].[Na+] | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[O;D1;H1:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C:2](-[O;D1;H1:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | A mixture of 1.8 g (14.7 mmoles) 3-chlorolactic acid and 3.4 g p-chlorophenol in 15 ml 3.3N sodium hydroxide was stirred under reflux for two hours. The mixture was cooled to room temperature and acidified to pH=3, with concentrated hydrochloric acid. The resulting white crystals were filtered and dissolved in hot wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | [OH-].[Na+] | null | null | O=C(O)C(O)CCl.Oc1ccc(Cl)cc1>[OH-].[Na+]>O=C(O)C(O)COc1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-049f17bf09a5437991fcb4535a89d071 | NNc1nc2ccccc2s1.O=C(CCCO)CC(=O)c1ccc(Cl)cc1>>OCCCC1=NN(c2nc3ccccc3s2)C(O)(c2ccc(Cl)cc2)C1 | ClC1=CC=C(C=C1)C(CC(CCCO)=O)=O.N(N)C=1SC2=C(N1)C=CC=C2>>S1C(=NC2=C1C=CC=C2)N2N=C(CC2(O)C2=CC=C(C=C2)Cl)CCCO | [NH2:6][NH:7][c:8]1[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[s:16]1.O=[C:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH2:26][C:17](=[O:18])[c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]1>>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1=[N:6][N:7]([c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[s:16]2)[C:17]([OH:18])([c:19]2[cH:2... | NNc1nc2ccccc2s1.O=C(CCCO)CC(=O)c1ccc(Cl)cc1 | OCCCC1=NN(c2nc3ccccc3s2)C(O)(c2ccc(Cl)cc2)C1 | null | null | CO.N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 300e37964a1e2b85b929af655bbc69ca70bf68448d8aafa9fb248125f32f80f2 | 6a48014694d6eed3cb5b40ee5b7ad219f45ef964e5cf9b1428542e30f6185946 | C1=NN(c2nc3ccccc3s2)C(c2ccccc2)C1 | O=[C;H0;D3;+0:1](-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7])-[C:8]-[C:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c:12]1:[#16;a:13]:[c:14]:[c:15]:[#7;a:16]:1>>[C:9]-[C:8]-[C;H0;D3;+0:1]1=[N;H0;D2;+0:10]-[N;H0;D3;+0:11](-[c:12]2:[#16;a:13]:[c:14]:[c:15]:[#7;a:16]:2)-[C;H0;D4;+0:3](-[OH;D1;+0:4])(-[c:5](:[c:6]):[c:7... | null | [] | null | null | 48 | HOUR | 6-(4-Chlorophenyl)-4,6-diketohexanol (7.2 g, 30 mM) was treated with 2-hydrazinobenzothiazole (4.96 g, 30 mM) in pyridine (5 ml) and MeOH (150 ml) at reflux for 2 hr and then allowed to stand at RT for 48 hr. The solvents were removed in vacuo and the crude residue purified by flash chromatography on silica with Et2O:E... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Hydrazone.Tertiary alcohol | null | C1=N[NH]CC1 | C1=N[NH]CC1.c1ccc2scnc2c1.c1ccccc1 | HO- | CO.N1=CC=CC=C1 | null | 48 | NNc1nc2ccccc2s1.O=C(CCCO)CC(=O)c1ccc(Cl)cc1>CO.N1=CC=CC=C1>OCCCC1=NN(c2nc3ccccc3s2)C(O)(c2ccc(Cl)cc2)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c264e2331d7b4273ae53b165f3a42301 | COc1ccc2nc(NN)sc2c1.O=C(CCCO)CC(=O)c1ccc(Cl)cc1>>COc1ccc2nc(-n3nc(CCCO)cc3-c3ccc(Cl)cc3)sc2c1 | ClC1=CC=C(C=C1)C(CC(CCCO)=O)=O.N(N)C=1SC2=C(N1)C=CC(=C2)OC>>ClC1=CC=C(C=C1)C1=CC(=NN1C=1SC2=C(N1)C=CC(=C2)OC)CCCO | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH:9][NH2:10])[s:25][c:26]2[cH:27]1.O=[C:11]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:16][C:17](=O)[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8](-[n:9]3[n:10][c:11]([CH2:12][CH2:13][CH2:14][OH:15])[cH:16][c:17]3-[c:18]3[cH... | COc1ccc2nc(NN)sc2c1.O=C(CCCO)CC(=O)c1ccc(Cl)cc1 | COc1ccc2nc(-n3nc(CCCO)cc3-c3ccc(Cl)cc3)sc2c1 | null | null | CO.N1=CC=CC=C1 | Aromatic Heterocycle Formation | Pyrazole formation | a567e118bc5ec031a47903b4ca0f0ab4ee21bde70a764fa379548bc1615cdb85 | d14f370ee7ee5e4a5c5c7412f191c74a005faab09898998e0db4b3670a6f4f81 | c1ccc(-c2ccnn2-c2nc3ccccc3s2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[NH2;D1;+0:11]-[NH;D2;+0:12]-[c;H0;D3;+0:13]1:[#16;a:14]:[c:15]:[c:16]:[#7;a:17]:1>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[n;H0;D3;+0:12](-[c;H0;D3;+0:1... | 80.9 | [{"value": 80.9, "product": "ClC1=CC=C(C=C1)C1=CC(=NN1C=1SC2=C(N1)C=CC(=C2)OC)CCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(4-Chlorophenyl)-4,6-diketohexanol (14.43 g, 60 mM) was treated with 2-hydrazino-6-methoxybenzothiazole (11.72 g, 60 mM) in pyridine (10 ml) and MeOH (300 ml) at reflux for 72 hr. Work-up as described in Example 1 followed by recrystallization from MeOH afforded the title compound 6 as a white solid (19.4 g), mp=123°... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | null | null | c1cc[nH]n1 | c1ccc2scnc2c1.c1cc[nH]n1.c1ccccc1 | HO- | CO.N1=CC=CC=C1 | null | null | COc1ccc2nc(NN)sc2c1.O=C(CCCO)CC(=O)c1ccc(Cl)cc1>CO.N1=CC=CC=C1>COc1ccc2nc(-n3nc(CCCO)cc3-c3ccc(Cl)cc3)sc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cbbe96bf61684243a07da170a8302318 | COc1ccc(NN)cc1.O=C(O)CCC(=O)CC(=O)c1cccnc1>>COc1ccc(-n2nc(CCC(=O)O)cc2-c2cccnc2)cc1 | Cl.COC1=CC=C(C=C1)NN.O=C(CCC(=O)O)CC(C=1C=NC=CC1)=O.CCN(CC)CC>>Cl.COC1=CC=C(C=C1)N1N=C(C=C1C=1C=NC=CC1)CCC(=O)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][NH2:8])[cH:23][cH:24]1.O=[C:9]([CH2:10][CH2:11][C:12](=[O:13])[OH:14])[CH2:15][C:16](=O)[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[n:8][c:9]([CH2:10][CH2:11][C:12](=[O:13])[OH:14])[cH:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][n:21][cH... | COc1ccc(NN)cc1.O=C(O)CCC(=O)CC(=O)c1cccnc1 | COc1ccc(-n2nc(CCC(=O)O)cc2-c2cccnc2)cc1 | null | null | CO | Aromatic Heterocycle Formation | Pyrazole formation | a567e118bc5ec031a47903b4ca0f0ab4ee21bde70a764fa379548bc1615cdb85 | d14f370ee7ee5e4a5c5c7412f191c74a005faab09898998e0db4b3670a6f4f81 | c1ccc(-n2nccc2-c2cccnc2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=O)-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8])-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1.[NH2;D1;+0:15]-[NH;D2;+0:16]-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:20]:[c:21]>>[O;D1;H0:7]=[C:6](-[O;D1;H1:8])-[C:5]-[C:4]-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;... | 52 | [{"value": 52.0, "product": "Cl.COC1=CC=C(C=C1)N1N=C(C=C1C=1C=NC=CC1)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.0, "product": "Cl.COC1=CC=C(C=C1)N1N=C(C=C1C=1C=NC=CC1)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 29 (2.21 g, 10 mM) in methanol (150 ml) containing Et3N (2 ml) was treated with 4-methoxyphenylhydrazine hydrochloride (1.85 g, 10.6 mM) at RT for 4 hr. The solvent was removed in vacuo and the residue was partitioned between 5% NaOH and Et2O. The basic aqueous layer was separated and acidified with 10% HCl to... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | null | null | c1cc[nH]n1 | c1ccccc1.c1cc[nH]n1.c1ccncc1 | HO- | CO | null | null | COc1ccc(NN)cc1.O=C(O)CCC(=O)CC(=O)c1cccnc1>CO>COc1ccc(-n2nc(CCC(=O)O)cc2-c2cccnc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8a523d4abd2d452793523bb1a14f206d | CN(C)C=O.COc1ccc(-n2nc(CCC(=O)O)cc2-c2cccnc2)cc1.O=C(Cl)C(=O)Cl>>COc1ccc(-n2nc(CCC(=O)N(C)O)cc2-c2cccnc2)cc1.O=CO | Cl.COC1=CC=C(C=C1)N1N=C(C=C1C=1C=NC=CC1)CCC(=O)O.CN(C)C=O.C(C(=O)Cl)(=O)Cl>>C(=O)O.ON(C(CCC1=NN(C(=C1)C=1C=NC=CC1)C1=CC=C(C=C1)OC)=O)C | C[N:14]([CH3:15])[CH:28]=[O:27].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[n:8][c:9]([CH2:10][CH2:11][C:12](=[O:13])[OH:29])[cH:17][c:18]2-[c:19]2[cH:20][cH:21][cH:22][n:23][cH:24]2)[cH:25][cH:26]1.O=C(Cl)C(Cl)=[O:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[n:8][c:9]([CH2:10][CH2:11][C:12](=[O:13])[N:14]([CH3:15]... | CN(C)C=O.COc1ccc(-n2nc(CCC(=O)O)cc2-c2cccnc2)cc1.O=C(Cl)C(=O)Cl | COc1ccc(-n2nc(CCC(=O)N(C)O)cc2-c2cccnc2)cc1.O=CO | null | null | C(Cl)Cl | Acylation | OtherReaction | d1e58bbc5f971c1c4d8248bc003ebf990c02002060e4fe6e6e9cde160f20e405 | 12abdd7911711032d2919d1877df33ddcc12a47bfd29cf527b34be50b6697704 | c1ccc(-n2nccc2-c2cccnc2)cc1 | C-[N;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D2;+0:3]=[O;D1;H0:4].Cl-C(=O)-C(-Cl)=[O;H0;D1;+0:5].[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[N;H0;D3;+0:1](-[C;D1;H3:2])-[OH;D1;+0:5].[O;D1;H0:4]=[CH;D2;+0:3]-[OH;D1;+0:10] | null | [] | null | null | 0.5 | HOUR | To a solution of compound 31 (0.9 g, 2 5 mM) in CH2Cl2 (25 ml) at RT was added DMF (0.2 ml) and oxalyl chloride (1.26 g, 10 mM). After stirring for 0.5 hr, the reaction mixture was evaporated in vacuo, redissolved in CH2Cl2 (25 ml) and added dropwise to a solution of methylhydroxylamine hydrochloride (0.84 g, 10 mM) an... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid.Tertiary amide | Carboxylic acid.Tertiary amide | null | null | c1ccccc1.c1cc[nH]n1.c1ccncc1 | HCl | C(Cl)Cl | null | 0.5 | CN(C)C=O.COc1ccc(-n2nc(CCC(=O)O)cc2-c2cccnc2)cc1.O=C(Cl)C(=O)Cl>C(Cl)Cl>COc1ccc(-n2nc(CCC(=O)N(C)O)cc2-c2cccnc2)cc1.O=CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e0f6b927331840ff8925668d568d22be | Cc1cc(OCCOCC2CC2)ccc1O.ClCC1CO1>>Cc1cc(OCCOCC2CC2)ccc1OCC1CO1 | C1(CC1)COCCOC1=CC(=C(C=C1)O)C.C(Cl)C1CO1.N1CCCCC1.C1(CC1)CBr>>CC1=C(C=CC(=C1)OCCOCC1CC1)OCC1CO1 | [CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH:10]2[CH2:11][CH2:12]2)[cH:13][cH:14][c:15]1[OH:16].Cl[CH2:17][CH:18]1[CH2:19][O:20]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH:10]2[CH2:11][CH2:12]2)[cH:13][cH:14][c:15]1[O:16][CH2:17][CH:18]1[CH2:19][O:20]1 | Cc1cc(OCCOCC2CC2)ccc1O.ClCC1CO1 | Cc1cc(OCCOCC2CC2)ccc1OCC1CO1 | null | [Pd] | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cc(OCC2CO2)ccc1OCCOCC1CC1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | null | [] | null | null | null | null | The epoxide starting material is obtained from reaction of 4-hydroxy-3-methylphenyl benzoate with benzyl bromide to give 4-benzyloxy-3-methylphenyl benzoate (M.P. 120°-121° from methanol/ether), followed by de-esterification with 2M NaOH solution to give 4-benzyloxy-3-methylphenol (M.P. 69°-70° from ether/hexane) and r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC1.C1CO1 | HCl | [Pd].O1CCCC1 | null | null | Cc1cc(OCCOCC2CC2)ccc1O.ClCC1CO1>[Pd].O1CCCC1>Cc1cc(OCCOCC2CC2)ccc1OCC1CO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d2ec217660cc426890ed2fa968b89793 | CCCOCCBr.COc1ccc(O)cc1F>>CCCOCCOc1ccc(OC)c(F)c1 | FC=1C=C(C=CC1OC)O.BrCCOCCC>>FC1=C(C=CC(=C1)OCCOCCC)OC | Br[CH2:6][CH2:5][O:4][CH2:3][CH2:2][CH3:1].[OH:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]1>>[CH3:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]1 | CCCOCCBr.COc1ccc(O)cc1F | CCCOCCOc1ccc(OC)c(F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | The epoxide starting material is obtained by reacting 3-fluoro-4-methoxyphenol with 1-bromo-2-propoxyethane. After work up of the reaction mixture 2-fluoro-1-methoxy-4-(2-propoxyethoxy)benzene is obtained which is then reacted with sodium thioethoxide giving 2-fluoro-4-(2-propoxyethoxy)phenol which is then reacted with... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | null | null | null | CCCOCCBr.COc1ccc(O)cc1F>>CCCOCCOc1ccc(OC)c(F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b4b66372e1674802b036ba6406a0f4d5 | CCCOCCBr.Oc1ccc(O)c(-c2ccccc2COCc2ccccc2-c2cc(O)ccc2O)c1>>CCCOCCOc1ccc(OCc2ccccc2)cc1 | C=1(O)C(=CC(O)=CC1)C1=CC=CC=C1COCC1=CC=CC=C1C=1C(O)=CC=C(C1)O.BrCCOCCC.[OH-].[Na+]>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)OCCOCCC | Br[CH2:6][CH2:5][O:4][CH2:3][CH2:2][CH3:1].Oc1ccc(O)c(-c2ccccc2CO[CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2-[c:20]2[c:11]([OH:12])[cH:10][cH:9][c:8]([OH:7])[cH:21]2)c1>>[CH3:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]... | CCCOCCBr.Oc1ccc(O)c(-c2ccccc2COCc2ccccc2-c2cc(O)ccc2O)c1 | CCCOCCOc1ccc(OCc2ccccc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 9da01df2c5e94e77402332204a1d42e796388de93cd56de94d069ed28033f8d0 | f2e26de4e1ba6b5a32a5fe55dbe7150f16fba038699ae952720d419cd82c7c54 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].O-c1:c:c:c(-O):c(-c2:c:c:c:c:c:2-C-O-[CH2;D2;+0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[c;H0;D3;+0:8]2:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]:[c:13]:[c:14]:2-[OH;D1;+0:15]):[c:16]:[c:17]):c:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:10]1:[c:9]:[cH;D2;+0:8]:[c:14](-[O;H0;D2;+0:15]-[CH2;D2;+0:4... | null | [] | null | null | null | null | Hydroquinone monobenzyl ether is reacted with 2-bromoethyl-n-propyl ether in aqueous sodium hydroxide and then purified over silica gel with toluene as eluent. The middle fraction gives 1-benzyloxy-4-(2-propoxy-ethoxy)benzene (used without further purification).
Conditions: See reaction.notes.procedure_details.
Workup:... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | Ether.Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | null | null | null | CCCOCCBr.Oc1ccc(O)c(-c2ccccc2COCc2ccccc2-c2cc(O)ccc2O)c1>>CCCOCCOc1ccc(OCc2ccccc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3f1ba7546b9c42598686538126fd8e3a | ClCC1CO1.Oc1ccc(OCc2ccccc2)cc1F>>Fc1cc(OCc2ccccc2)ccc1OCC1CO1 | C(C1=CC=CC=C1)OC1=CC(=C(C=C1)O)F.C(Cl)C1CO1.N1CCCCC1>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)OCC1CO1)F | Cl[CH2:17][CH:18]1[CH2:19][O:20]1.[F:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15]1[OH:16]>>[F:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15]1[O:16][CH2:17][CH:18]1[CH2:19][O:20]1 | ClCC1CO1.Oc1ccc(OCc2ccccc2)cc1F | Fc1cc(OCc2ccccc2)ccc1OCC1CO1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccc(OCC3CO3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | null | [] | null | null | 1 | HOUR | 4.0 g of 4-benzyloxy-2-fluorophenol is reacted with 10 g epichlorhydrin and 0.2 ml piperidine for 90 minutes at 100°. After removal of the volatile material, 40 ml tetrahydrofuran and 20 ml 2M NaOH is added. After 1 hour stirring the solvent is evaporated and the residue partitioned between methylenechloride and water.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.C1CO1 | HCl | null | null | 1 | ClCC1CO1.Oc1ccc(OCc2ccccc2)cc1F>>Fc1cc(OCc2ccccc2)ccc1OCC1CO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8b03c4b147cc4e73961cfb46cd3fddcd | CCCCc1nc2cccc(C)c2[nH]1.O=[N+]([O-])c1ccc(CBr)cc1>>CCCCc1nc2c(C)cccc2n1Cc1ccc([N+](=O)[O-])cc1 | [H-].[Na+].[N+](=O)([O-])C1=CC=C(CBr)C=C1.C(CCC)C=1NC2=C(N1)C=CC=C2C>>C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)[N+](=O)[O-])C=CC=C2C | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[nH:6][c:7]2[c:8]([CH3:9])[cH:10][cH:11][cH:12][c:13]2[n:14]1.Br[CH2:15][c:16]1[cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([CH3:9])[cH:10][cH:11][cH:12][c:13]2[n:14]1[CH2:15][c:16]1[cH:17][cH:18][c:19]([N+:20](=[O:21]... | CCCCc1nc2cccc(C)c2[nH]1.O=[N+]([O-])c1ccc(CBr)cc1 | CCCCc1nc2c(C)cccc2n1Cc1ccc([N+](=O)[O-])cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 798c3cd6443cfe7f029ed03c4760cf76103b5f272c5de707760a27469f565eca | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2cnc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[n;H0;D2;+0:7]:[c:8](:[c:9]):[c:10](:[c:11]):[nH;D2;+0:12]:1>>[C:5]-[c:6]1:[n;H0;D2;+0:12]:[c:10](:[c:11]):[c:8](:[c:9]):[n;H0;D3;+0:7]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 87.5 | [{"value": 87.5, "product": "C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)[N+](=O)[O-])C=CC=C2C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a slurry of NaH (60%, 0.21 g. 5.3 mmol) in DMF was added with stirring a solution of 2-butyl-4-methyl-benzimidazole (1 g. 5.3 mmol) in DMF (20 mL under nitrogen atmosphere. After the gas evolution was complete, the reaction mixture was cooled in ice and a solution of 4-nitrobenzyl bromide (1.5 g, 5.3 mmol) in DMF (5... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1 | c1nc2ccccc2[nH]1.c1ccccc1 | HBr | CN(C)C=O | null | null | CCCCc1nc2cccc(C)c2[nH]1.O=[N+]([O-])c1ccc(CBr)cc1>CN(C)C=O>CCCCc1nc2c(C)cccc2n1Cc1ccc([N+](=O)[O-])cc1 |
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