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-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-55281f1cf81b44dc9b8868b0f77d3916 | CCCC(=O)Cl.O=C(O)CCCCCCCCCCCO>>CCCC(=O)OCCCCCCCCCCCC(=O)O | O.C(CCC)(=O)Cl.OCCCCCCCCCCCC(=O)O.C(Cl)(Cl)Cl>>C(CCC)(=O)OCCCCCCCCCCCC(=O)O | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[OH:20]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[OH:20] | CCCC(=O)Cl.O=C(O)CCCCCCCCCCCO | CCCC(=O)OCCCCCCCCCCCC(=O)O | null | null | N1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C:5] | 96.7 | [{"value": 96.7, "product": "C(CCC)(=O)OCCCCCCCCCCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 12-Hydroxydodecanoic acid (1 g) was dissolved in pyridine, and butyroyl chloride (0.59 g) was added to the solution in an ice bath. After 4 hours of stirring, the reaction mixture was distributed into chloroform and water, and the chloroform layer was concentrated to give 12-butyryloxydodecanoic acid (1.28 g).
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | null | HCl | N1=CC=CC=C1 | null | 4 | CCCC(=O)Cl.O=C(O)CCCCCCCCCCCO>N1=CC=CC=C1>CCCC(=O)OCCCCCCCCCCCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0254d0ce63fa471dba56770add46dffe | CS(=O)(=O)Cl.O=C(O)CCCCCCCCCCCCCCCO>>CS(=O)(=O)OCCCCCCCCCCCCCCCC(=O)O | OCCCCCCCCCCCCCCCC(=O)O.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCCCCCCCCCCCCCC(=O)O | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:22])[OH:23]>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C... | CS(=O)(=O)Cl.O=C(O)CCCCCCCCCCCCCCCO | CS(=O)(=O)OCCCCCCCCCCCCCCCC(=O)O | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 8 | HOUR | 16-Hydroxyhexadecanoic acid (1 g) dissolved in a 10% hydrochloric acid-methanol solution was stirred at room temperature for 1 hour. The mixture was then concentrated and distributed into chloroform and water, and the chloroform layer was washed with a 1% aqueous sodium hydrogen carbonate solution and water, dried with... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | N1=CC=CC=C1 | null | 8 | CS(=O)(=O)Cl.O=C(O)CCCCCCCCCCCCCCCO>N1=CC=CC=C1>CS(=O)(=O)OCCCCCCCCCCCCCCCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-952a4908bc264942b9d6c1ee7c2fdf0f | CCCS(=O)(=O)Cl.O=C(O)CCCCCCCCCCCO>>CCCS(=O)(=O)OCCCCCCCCCCCC(=O)O | C(Cl)(Cl)Cl.C(C)N(CC)CC.OCCCCCCCCCCCC(=O)O.C(CC)S(=O)(=O)Cl>>C(CC)S(=O)(=O)OCCCCCCCCCCCC(=O)O | Cl[S:4]([CH2:3][CH2:2][CH3:1])(=[O:5])=[O:6].[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:20])[OH:21]>>[CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:20])[OH:21] | CCCS(=O)(=O)Cl.O=C(O)CCCCCCCCCCCO | CCCS(=O)(=O)OCCCCCCCCCCCC(=O)O | null | null | O.C(Cl)(Cl)Cl.CCCCCC.C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 76a2f1ce13fb019af608455a0d79fe83b29c455d623b278b739d67e5b567ea89 | e7708aa65b3d8696add9aec26cae169160bb027d6d2772db2030dd9c0b07b540 | null | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:8]-[C:7]-[C:6] | null | [] | null | null | null | null | 12-Hydroxydodecanoic acid (1 g) was dissolved in methylene chloride (25 ml), and triethylamine (2 ml) was added to the solution. To the mixture, while it was ice-cooled and stirred, was added dropwise 1-propanesulfonyl chloride (1.03 ml). After 1.5 hours of stirring, the reaction mixture was distributed into chloroform... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfonate | null | null | null | HCl | O.C(Cl)(Cl)Cl.CCCCCC.C(Cl)Cl | null | null | CCCS(=O)(=O)Cl.O=C(O)CCCCCCCCCCCO>O.C(Cl)(Cl)Cl.CCCCCC.C(Cl)Cl>CCCS(=O)(=O)OCCCCCCCCCCCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0cb8cf42c51d483c90e843db18c5d727 | CCCCS(=O)(=O)Cl.O=C(O)CCCCCCCCCCCO>>CCCCS(=O)(=O)OCCCCCCCCCCCC(=O)O | C(Cl)(Cl)Cl.C(C)N(CC)CC.OCCCCCCCCCCCC(=O)O.C(CCC)S(=O)(=O)Cl>>C(CCC)S(=O)(=O)OCCCCCCCCCCCC(=O)O | Cl[S:5]([CH2:4][CH2:3][CH2:2][CH3:1])(=[O:6])=[O:7].[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[OH:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][S:5](=[O:6])(=[O:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O... | CCCCS(=O)(=O)Cl.O=C(O)CCCCCCCCCCCO | CCCCS(=O)(=O)OCCCCCCCCCCCC(=O)O | null | null | O.C(Cl)(Cl)Cl.CCCCCC.C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 76a2f1ce13fb019af608455a0d79fe83b29c455d623b278b739d67e5b567ea89 | e7708aa65b3d8696add9aec26cae169160bb027d6d2772db2030dd9c0b07b540 | null | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5] | null | [] | null | null | null | null | 12-Hydroxydodecanoic acid (1 g) was dissolved in methylene chloride (25 ml), and triethylamine (2 ml) was added to the solution. To the mixture, while it was ice-cooled and stirred, was added dropwise 1-butanesulfonyl chloride (0.72 ml). After 1.5 hours of stirring, the reaction mixture was distributed into chloroform ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfonate | null | null | null | HCl | O.C(Cl)(Cl)Cl.CCCCCC.C(Cl)Cl | null | null | CCCCS(=O)(=O)Cl.O=C(O)CCCCCCCCCCCO>O.C(Cl)(Cl)Cl.CCCCCC.C(Cl)Cl>CCCCS(=O)(=O)OCCCCCCCCCCCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d865f6537bee4af98d82b0b8f1ae0c5b | CCCCCCCCCCC(O)C(=O)O.CCCCS(=O)(=O)Cl>>CCCCCCCCCCC(OS(=O)(=O)CCCC)C(=O)O | OC(C(=O)O)CCCCCCCCCC.C(CCC)S(=O)(=O)Cl>>C(CCC)S(=O)(=O)OC(C(=O)O)CCCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:12])[C:20](=[O:21])[OH:22].Cl[S:13](=[O:14])(=[O:15])[CH2:16][CH2:17][CH2:18][CH3:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([O:12][S:13](=[O:14])(=[O:15])[CH2:16][CH2:17][CH2:18][CH3:19])[C:20](=... | CCCCCCCCCCC(O)C(=O)O.CCCCS(=O)(=O)Cl | CCCCCCCCCCC(OS(=O)(=O)CCCC)C(=O)O | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | c184cd9c1ecb8822b9c113081558d8b3ee6833d6da62159d9b187f5f9739f3d9 | 89e1ad72f771160c1b3f894db16d20f6bb502317406ac4d2d61d0e3463ed10b3 | null | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[C:6]-[C:7](-[OH;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[C:6]-[C:7](-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | null | [] | null | null | 8 | HOUR | 2-Hydroxydodecanoic acid (1 g) dissolved in a 10% methanolic hydrochloric acid solution was stirred at room temperature for 1 hour. The mixture was then concentrated and distributed into chloroform and water, and the chloroform layer was washed with a 1% aqueous sodium hydrogen carbonate solution and water, dried with ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Sulfonate | null | null | null | HCl | N1=CC=CC=C1 | null | 8 | CCCCCCCCCCC(O)C(=O)O.CCCCS(=O)(=O)Cl>N1=CC=CC=C1>CCCCCCCCCCC(OS(=O)(=O)CCCC)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a84d1f355c03410da2b6036f00decac0 | C[Si](C)(C)C#CCCCCCCCCC(=O)O>>C[Si](C)(C)CCCCCCCCCCC(=O)O | C[Si](C#CCCCCCCCCC(=O)O)(C)C>>C[Si](CCCCCCCCCCC(=O)O)(C)C | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:16])[OH:17]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:16])[OH:17] | C[Si](C)(C)C#CCCCCCCCCC(=O)O | C[Si](C)(C)CCCCCCCCCCC(=O)O | null | [C].[Pd] | C(C)(=O)OCC | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8] | 89.9 | [{"value": 89.9, "product": "C[Si](CCCCCCCCCCC(=O)O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | At the same time, 11-trimethylsilyl-10-undecynoic acid (0.23 g) was dissolved in ethyl acetate (5 ml), and 10% palladium-carbon (10 mg) was added to the solution. After the air within the reactor was purged with hydrogen, the mixture was stirred at room temperature for 12 hours. Then, the mixture was filtered, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | null | null | [C].[Pd].C(C)(=O)OCC | null | 12 | C[Si](C)(C)C#CCCCCCCCCC(=O)O>[C].[Pd].C(C)(=O)OCC>C[Si](C)(C)CCCCCCCCCCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ad96952fa66649908af6ba02acd03169 | CCCCCCCC/C=C\CCCCCCCC(=O)O.O=S(O)O.[O]=[Mn](=[O])(=[O])[O-]>>CCCCCCCCC(O)C(O)CCCCCCCC(=O)O | S(O)(O)=O.[OH-].[Na+].C(CCCCCCC\C=C/CCCCCCCC)(=O)O.[Mn](=O)(=O)(=O)[O-].[K+]>>OC(CCCCCCCC(=O)O)C(CCCCCCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:11]\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[OH:22].O=S(O)[OH:10].[O]=[Mn](=[O])(=[O])[O-:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([OH:10])[CH:11]([OH:12])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17... | CCCCCCCC/C=C\CCCCCCCC(=O)O.O=S(O)O.[O]=[Mn](=[O])(=[O])[O-] | CCCCCCCCC(O)C(O)CCCCCCCC(=O)O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | d8b358923bac0b4eda3a0bb6ca0d2330712a9c50bd67727f91eae83695d1e78a | f06606da6294c35122c48d971bcac1ac3dd1d28bcdc6f95c150d168954e4f501 | null | O-S(=O)-[OH;D1;+0:1].[C:2]-[C:3]/[CH;D2;+0:4]=[CH;D2;+0:5]\[C:6]-[C:7].[O-;H0;D1:8]-[Mn](=[O])(=[O])=[O]>>[C:2]-[C:3]-[CH;D3;+0:4](-[OH;D1;+0:8])-[CH;D3;+0:5](-[OH;D1;+0:1])-[C:6]-[C:7] | 84.4 | [{"value": 84.4, "product": "OC(CCCCCCCC(=O)O)C(CCCCCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | null | null | To a solution of NaOH (5.03 g) in water (200 ml) was suspended oleic acid (4.96 g), and the mixture to which ice had been added, was stirred at 5° C. A solution of potassium permanganate (4 g) in water (500 ml) was added, and the mixture was stirred for 5 minutes. Then, aqueous sulfurous acid was added until the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary alcohol.Secondary alcohol | null | null | null | Other | O | 5 | null | CCCCCCCC/C=C\CCCCCCCC(=O)O.O=S(O)O.[O]=[Mn](=[O])(=[O])[O-]>O>CCCCCCCCC(O)C(O)CCCCCCCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-70204ee594074200bc8d18e226f7c994 | CCCCCCCCCCCCCCCCC(O)C(=O)O>>CCCCCCC(=O)CCCCCCCCCCC(=O)O | OC(C(=O)O)CCCCCCCCCCCCCCCC.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>O=C(CCCCCCCCCCC(=O)O)CCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([OH:8])[C:19](=[O:20])[OH:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:20])[OH:21] | CCCCCCCCCCCCCCCCC(O)C(=O)O | CCCCCCC(=O)CCCCCCCCCCC(=O)O | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | bfff098c086bbc8bb05a0961fd38d70b4ef5b97280d07cd012243548d9ac1fe8 | ef59ba7fad669d0d82c4daf03280dc0366c9a31cf6192836b4997e72f66f9d7c | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[C:4]-[C:5].[C:6]-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:9])-[C:4]-[C:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12] | 90.6 | [{"value": 90.6, "product": "O=C(CCCCCCCCCCC(=O)O)CCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 12-Hydroxystearic acid (2 g) dissolved in a 10% methanolic hydrochloric acid solution was stirred at room temperature for 2 hours. The mixture was then concentrated and distributed into chloroform and water, and the chloroform layer was washed with a 1% aqueous sodium hydrogen carbonate solution and water, dried with a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | null | null | C(Cl)Cl | null | 24 | CCCCCCCCCCCCCCCCC(O)C(=O)O>C(Cl)Cl>CCCCCCC(=O)CCCCCCCCCCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-348485e64166449e857ebc7ebe4eeff6 | CC(C)CCCCCCCCCC(=O)O>>CC(C)CCCCCCCCC(=O)O | CC(CCCCCCCCCC(=O)O)C.[N+](=O)([O-])C1=CC=C(C=C1)O.C1(CCCCC1)N=C=NC1CCCCC1>>CC(CCCCCCCCC(=O)O)C | C([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:9][CH2:10][CH2:11][C:12](=[O:13])[OH:14]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[OH:14] | CC(C)CCCCCCCCCC(=O)O | CC(C)CCCCCCCCC(=O)O | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [C:1]-[C:2]-[CH2;D2;+0:3]-C-[CH2;D2;+0:4]-[C:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | null | null | 12 | HOUR | To 11-methyldodecanoic acid (400 mg) and para-nitrophenol (260 mg) dissolved in N,N-dimethylformamide (DMF, 30 ml) was added N,N'-dicyclohexylcarbodiimide (385 mg), and the mixture was stirred for 12 hours. The reaction mixture was filtered and concentrated to give the active ester of 10-methylundecanoic acid. To the a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | CN(C=O)C | null | 12 | CC(C)CCCCCCCCCC(=O)O>CN(C=O)C>CC(C)CCCCCCCCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3c286fd877f34f879bc81d1930a9e7b0 | CCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCCC/C=C/C=C/C(=O)O | CCCCCC.C(C)(=O)OCC.C(\C=C\CCCCCCC)=O.C(=O)(OC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(\C=C\C=C\CCCCCCC)(=O)O | O=[CH:10]/[CH:9]=[CH:8]/[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].C[O:14][C:12]([CH:11]=P(c1ccccc1)(c1ccccc1)c1ccccc1)=[O:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]/[CH:10]=[CH:11]/[C:12](=[O:13])[OH:14] | CCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCCC/C=C/C=C/C(=O)O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 6b3c0eb3ed6d44a9f973c5f4266e84250e8ebf5a1d1e0860ef8cdbe9a0241cc8 | 0aab88bc004204544a4ed5a027815bc5384a304c50cca0b067c18dd1842afcf6 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:5]/[C:6]=[C:7]/[C:8]-[C:9]>>[C:9]-[C:8]/[C:7]=[C:6]/[CH;D2;+0:5]=[CH;D2;+0:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 2 | HOUR | To trans-2-decenal (5.0 g) dissolved in methylene chloride (80 ml) was added (carbomethoxymethylene)-triphenylphosphorane (11.99 g), and the mixture was stirred for 2 hours. The reaction mixture was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 20:1) to ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Carboxylic acid.Conjugated diene | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | C(Cl)Cl | null | 2 | CCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)Cl>CCCCCCC/C=C/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-08ed0b0826304321ab3cd4a08246e2c5 | CCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCCCC/C=C/C=C/C(=O)O | CCCCCC.C(C)(=O)OCC.C(\C=C\CCCCCCCC)=O.C(=O)(OC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(\C=C\C=C\CCCCCCCC)(=O)O | O=[CH:11]/[CH:10]=[CH:9]/[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].C[O:15][C:13]([CH:12]=P(c1ccccc1)(c1ccccc1)c1ccccc1)=[O:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[C:13](=[O:14])[OH:15] | CCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCCCC/C=C/C=C/C(=O)O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 6b3c0eb3ed6d44a9f973c5f4266e84250e8ebf5a1d1e0860ef8cdbe9a0241cc8 | 0aab88bc004204544a4ed5a027815bc5384a304c50cca0b067c18dd1842afcf6 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:5]/[C:6]=[C:7]/[C:8]-[C:9]>>[C:9]-[C:8]/[C:7]=[C:6]/[CH;D2;+0:5]=[CH;D2;+0:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 2 | HOUR | To trans-2-undecenal (5.0 g) dissolved in methylene chloride (80 ml) was added (carbomethoxymethylene)-triphenylphosphorane (9.9 g), and the mixture was stirred for 2 hours. The reaction mixture was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 20:1) to ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Carboxylic acid.Conjugated diene | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | C(Cl)Cl | null | 2 | CCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)Cl>CCCCCCCC/C=C/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0b6f64cb017c475b8c1f51c233981126 | CCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCCCCC/C=C/C=C/C(=O)O | CCCCCC.C(C)(=O)OCC.C(\C=C\CCCCCCCCC)=O.C(=O)(OC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(\C=C\C=C\CCCCCCCCC)(=O)O | O=[CH:12]/[CH:11]=[CH:10]/[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].C[O:16][C:14]([CH:13]=P(c1ccccc1)(c1ccccc1)c1ccccc1)=[O:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14](=[O:15])[OH:16] | CCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCCCCC/C=C/C=C/C(=O)O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 6b3c0eb3ed6d44a9f973c5f4266e84250e8ebf5a1d1e0860ef8cdbe9a0241cc8 | 0aab88bc004204544a4ed5a027815bc5384a304c50cca0b067c18dd1842afcf6 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:5]/[C:6]=[C:7]/[C:8]-[C:9]>>[C:9]-[C:8]/[C:7]=[C:6]/[CH;D2;+0:5]=[CH;D2;+0:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 2 | HOUR | To trans-2-dodecenal (4.5 g) dissolved in methylene chloride (80 ml) was added (carbomethoxymethylene)-triphenylphosphorane (8.3 g), and the mixture was stirred for 2 hours. The reaction mixture was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 20:1) to ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Carboxylic acid.Conjugated diene | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | C(Cl)Cl | null | 2 | CCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)Cl>CCCCCCCCC/C=C/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-773530b0f31d431ab66ac2066c4c32fa | CCCCCCCCC/C=C/C=C/C(=O)Cl.NCC(=O)O>>CCCCCCCCC/C=C/C=C/C(=O)NCC(=O)O | NCC(=O)O.C(\C=C\C=C\CCCCCCCCC)(=O)Cl.Cl>>C(\C=C\C=C\CCCCCCCCC)(=O)NCC(=O)O | Cl[C:14](/[CH:13]=[CH:12]/[CH:11]=[CH:10]/[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:15].[NH2:16][CH2:17][C:18](=[O:19])[OH:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14](=[O:15])[NH:16][CH2:17][C:18](=[O:19])[OH:20] | CCCCCCCCC/C=C/C=C/C(=O)Cl.NCC(=O)O | CCCCCCCCC/C=C/C=C/C(=O)NCC(=O)O | null | null | [OH-].[Na+] | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[C:5]=[C:6]/[C:7].[NH2;D1;+0:8]-[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[C:7]/[C:6]=[C:5]/[C:4]=[C:3]/[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12] | 63.4 | [{"value": 63.4, "product": "C(\\C=C\\C=C\\CCCCCCCCC)(=O)NCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | In the second method, trans,trans-2,4-tetradecadienoic acid (99.6 g) was dissolved in thionyl chloride (87 ml), and the mixture was stirred at room temperature. The excessive thionyl chloride was removed by distillation to give trans,trans-2,4-tetradecadienoic acid chloride (102.0 g). To glycine (66.8 g) dissolved in a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HCl | [OH-].[Na+] | null | 0.25 | CCCCCCCCC/C=C/C=C/C(=O)Cl.NCC(=O)O>[OH-].[Na+]>CCCCCCCCC/C=C/C=C/C(=O)NCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b385d21dacc34112b3b773e7c6b5ce38 | CCCCCCCCCC/C=C/CO>>CCCCCCCCCC/C=C/C=O | C(\C=C\CCCCCCCCCC)O.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>C(\C=C\CCCCCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH2:13][OH:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH:13]=[O:14] | CCCCCCCCCC/C=C/CO | CCCCCCCCCC/C=C/C=O | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | null | [C:1]-[C:2]/[C:3]=[C:4]/[CH2;D2;+0:5]-[OH;D1;+0:6]>>[C:1]-[C:2]/[C:3]=[C:4]/[CH;D2;+0:5]=[O;H0;D1;+0:6] | null | [] | null | null | null | null | To undecyl aldehyde (5.0 g) dissolved in methylene chloride was added (carbomethoxymethylene)-triphenylphosphorane (14.7 g), and the mixture was stirred for 2 hours. The reaction mixture was concentrated and subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | null | C(Cl)Cl | null | null | CCCCCCCCCC/C=C/CO>C(Cl)Cl>CCCCCCCCCC/C=C/C=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-46102a0734cb4b7699b687bd2df63c73 | CCCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCCCCCC/C=C/C=C/C(=O)O | CCCCCC.C(C)(=O)OCC.C(\C=C\CCCCCCCCCC)=O.C(=O)(OC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(\C=C\C=C\CCCCCCCCCC)(=O)O | O=[CH:13]/[CH:12]=[CH:11]/[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].C[O:17][C:15]([CH:14]=P(c1ccccc1)(c1ccccc1)c1ccccc1)=[O:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH:13]=[CH:14]/[C:15](=[O:16])[OH:17] | CCCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCCCCCC/C=C/C=C/C(=O)O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 6b3c0eb3ed6d44a9f973c5f4266e84250e8ebf5a1d1e0860ef8cdbe9a0241cc8 | 0aab88bc004204544a4ed5a027815bc5384a304c50cca0b067c18dd1842afcf6 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:5]/[C:6]=[C:7]/[C:8]-[C:9]>>[C:9]-[C:8]/[C:7]=[C:6]/[CH;D2;+0:5]=[CH;D2;+0:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 2 | HOUR | To the trans-2-tridecenal (1.7 g) dissolved in methylene chloride (80 ml) was added (carbomethoxymethylene)triphenyl phosphorane (4.0 g), and the mixture was stirred for 2 hours. The reaction mixture was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 20:1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Carboxylic acid.Conjugated diene | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | C(Cl)Cl | null | 2 | CCCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)Cl>CCCCCCCCCC/C=C/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-23c3958dd87549e89d2ed3543b894d8e | C1CCOC1.CCOC(C)=O.O>>CCCCCCCCCCC/C=C/CO | O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.C(C)(=O)OCC>>C(\C=C\CCCCCCCCCCC)O | O1[CH2:3][CH2:4][CH2:5][CH2:6]1.O=[C:1](O[CH2:10][CH3:9])[CH3:8].[OH2:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][OH:15] | C1CCOC1.CCOC(C)=O.O | CCCCCCCCCCC/C=C/CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 02283909125dca70d9e0019466d585a180c95f4833c892afdf102c8ef5ff0851 | 1431ccec8782b63af0d868ed469b74b1ffcce77fcc3c4467b47de07d818b7296 | null | O1-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1.O=[C;H0;D3;+0:5](-[CH3;D1;+0:6])-O-[CH2;D2;+0:7]-[CH3;D1;+0:8].[OH2;D0;+0:9]>>[CH3;D1;+0:5]-[C:10]-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[C:11]-[CH2;D2;+0:6]-[CH2;D2;+0:8]-[CH2;D2;+0:7]-[C:12]/[C:13]=[C:14]/[C:15]-[OH;D1;+0:9] | null | [] | null | null | 1 | HOUR | To dodecyl aldehyde (5.0 g) dissolved in methylene chloride was added (carbomethoxymethylene)-triphenylphosphorane (9.1 g), and the mixture was stirred for 2 hours. The reaction mixture was concentrated and subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 2... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Primary alcohol | C1CCOC1 | null | null | null | null | null | 1 | C1CCOC1.CCOC(C)=O.O>>CCCCCCCCCCC/C=C/CO |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a88d7a552e57437ab087ba002016de0d | CCCCCCCCCC/C=C/CO>>CCCCCCCCCCC/C=C/C=O | C(\C=C\CCCCCCCCCC)O.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>C(\C=C\CCCCCCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH2:13][OH:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]/[CH:14]=[O:15] | CCCCCCCCCC/C=C/CO | CCCCCCCCCCC/C=C/C=O | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | c8f5aa755735a72c7bf36287d92584ced535c4052cf072fc77ee8ea418da9fe1 | f7f2afa3238e01577f917b922de7000377ac3719fad83b94ff019f8901a18e34 | null | [C:1]-[C:2]/[CH;D2;+0:3]=[CH;D2;+0:4]/[CH2;D2;+0:5]-[OH;D1;+0:6]>>[C:1]-[C:2]-[CH2;D2;+0:3]/[CH;D2;+0:4]=[CH;D2;+0:5]/[C:7]=[O;H0;D1;+0:6] | null | [] | null | null | null | null | To dodecyl aldehyde (5.0 g) dissolved in methylene chloride was added (carbomethoxymethylene)-triphenylphosphorane (9.1 g), and the mixture was stirred for 2 hours. The reaction mixture was concentrated and subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 2... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | Other | C(Cl)Cl | null | null | CCCCCCCCCC/C=C/CO>C(Cl)Cl>CCCCCCCCCCC/C=C/C=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1a519f79617f4944a520ab69770286f8 | CCCCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCCCCCCC/C=C/C=C/C(=O)O | CCCCCC.C(C)(=O)OCC.C(\C=C\CCCCCCCCCCC)=O.C(=O)(OC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(\C=C\C=C\CCCCCCCCCCC)(=O)O | O=[CH:14]/[CH:13]=[CH:12]/[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].C[O:18][C:16]([CH:15]=P(c1ccccc1)(c1ccccc1)c1ccccc1)=[O:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]/[CH:14]=[CH:15]/[C:16](=[O:17])[OH:18] | CCCCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCCCCCCC/C=C/C=C/C(=O)O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 6b3c0eb3ed6d44a9f973c5f4266e84250e8ebf5a1d1e0860ef8cdbe9a0241cc8 | 0aab88bc004204544a4ed5a027815bc5384a304c50cca0b067c18dd1842afcf6 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:5]/[C:6]=[C:7]/[C:8]-[C:9]>>[C:9]-[C:8]/[C:7]=[C:6]/[CH;D2;+0:5]=[CH;D2;+0:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 2 | HOUR | To the trans-2-tetradecenal (2.3 g) dissolved in methylene chloride (80 ml) was added (carbomethoxymethylene)triphenylphosphorane (4.4 g), and the mixture was stirred for 2 hours. The reaction mixture was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 20:... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Carboxylic acid.Conjugated diene | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | C(Cl)Cl | null | 2 | CCCCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)Cl>CCCCCCCCCCC/C=C/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-25ddcb12808146b0826d7a38ce15db0c | OCCCCCCCCCCCBr>>O=CCCCCCCCCCCBr | BrCCCCCCCCCCCO.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>BrCCCCCCCCCCC=O | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13] | OCCCCCCCCCCCBr | O=CCCCCCCCCCCBr | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 72 | [{"value": 72.0, "product": "BrCCCCCCCCCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To 11-bromo-1-undecanol (5 g) dissolved in methylene chloride (70 ml) were added pyridinium chlorochromate (10.7 g) and Celite (11.0 g), and the mixture was stirred at room temperature for 12 hours. Then, the reaction mixture was filtered, concentrated and subjected to chromatography on a silica gel column with an elue... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | null | C(Cl)Cl | null | 12 | OCCCCCCCCCCCBr>C(Cl)Cl>O=CCCCCCCCCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a8391727432442ce8221db62fa6a5273 | OCCCCCCCCCCCCBr>>O=CCCCCCCCCCCCBr | BrCCCCCCCCCCCCO.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>BrCCCCCCCCCCCC=O | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14] | OCCCCCCCCCCCCBr | O=CCCCCCCCCCCCBr | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 75 | [{"value": 75.0, "product": "BrCCCCCCCCCCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To 12-bromo-1-dodecanol (5 g) dissolved in methylene chloride (70 ml) were added pyridinium chlorochromate (10.1 g) and Celite (11.0 g), and the mixture was stirred at room temperature for 12 hours. Then, the reaction mixture was filtered, concentrated and subjected to chromatography on a silica gel column with an elue... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | null | C(Cl)Cl | null | 12 | OCCCCCCCCCCCCBr>C(Cl)Cl>O=CCCCCCCCCCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3bb4d314c9da4afc906ff780940b0630 | OCCCCCCCCCCCBr>>O=CCCCCCCCCCCBr | BrCCCCCCCCCCCO.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>BrCCCCCCCCCCC=O | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13] | OCCCCCCCCCCCBr | O=CCCCCCCCCCCBr | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 72 | [{"value": 72.0, "product": "BrCCCCCCCCCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To 11-bromo-1-undecanol (5 g) dissolved in methylene chloride (70 ml) were added pyridinium chlorochromate (10.7 g) and Celite (11.0 g), and the mixture was stirred at room temperature for 12 hours. Then, the reaction mixture was filtered, concentrated and subjected to chromatography on a silica gel column with an elue... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | null | C(Cl)Cl | null | 12 | OCCCCCCCCCCCBr>C(Cl)Cl>O=CCCCCCCCCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b8c71dc682e34eae85a13d03ec8a9f9a | OCCCCCCCCCCCCBr>>O=CCCCCCCCCCCCBr | BrCCCCCCCCCCCCO.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>BrCCCCCCCCCCCC=O | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14] | OCCCCCCCCCCCCBr | O=CCCCCCCCCCCCBr | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 75 | [{"value": 75.0, "product": "BrCCCCCCCCCCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To 12-bromo-1-dodecanol (5 g) dissolved in methylene chloride (70 ml) were added pyridinium chlorochromate (10.1 g) and Celite (11.0 g), and the mixture was stirred at room temperature for 12 hours. Then, the reaction mixture was filtered, concentrated and subjected to chromatography on a silica gel column with an elue... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | null | C(Cl)Cl | null | 12 | OCCCCCCCCCCCCBr>C(Cl)Cl>O=CCCCCCCCCCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7ccbd024eb7c423ea7a6406759a29db0 | OCCCCCCCCCCCCBr>>O=CCCCCCCCCCCCBr | BrCCCCCCCCCCCCO.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>BrCCCCCCCCCCCC=O | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14] | OCCCCCCCCCCCCBr | O=CCCCCCCCCCCCBr | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 88.7 | [{"value": 88.7, "product": "BrCCCCCCCCCCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To 12-bromododecanol (5 g) dissolved in methylene chloride (30 ml) were added Celite (5.0 g) and pyridinium chlorochromate (5.2 g), and the mixture was stirred at room temperature for 12 hours. Then, the reaction mixture was filtered and subjected to chromatography on a silica gel column with an eluent system of n-hexa... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | null | C(Cl)Cl | null | 12 | OCCCCCCCCCCCCBr>C(Cl)Cl>O=CCCCCCCCCCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-12e19c424de44218a3dc1d684f05dd8c | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCCCCCCCCCCCBr>>O=C(O)C=CCCCCCCCCCCCBr | CCCCCC.C(C)(=O)OCC.BrCCCCCCCCCCCC=O.C(=O)(OC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCCCCCCCCCCC=CC(=O)O | C[O:3][C:2](=[O:1])[CH:4]=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Br:17]>>[O:1]=[C:2]([OH:3])[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Br:17] | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCCCCCCCCCCCBr | O=C(O)C=CCCCCCCCCCCCBr | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | c06f441329a1c85dd58b67c3ed7dca4f2b4838e56125ed608c5d39ebec591cc0 | 04a7a14866317f7132eb69ea35ca8b6703c51b03c0c51c392001b195de1edfe7 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:5]-[C:6]-[C:7]>>[C:7]-[C:6]-[CH;D2;+0:5]=[CH;D2;+0:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 4 | HOUR | To 12-bromododecanol (5 g) dissolved in methylene chloride (30 ml) were added Celite (5.0 g) and pyridinium chlorochromate (5.2 g), and the mixture was stirred at room temperature for 12 hours. Then, the reaction mixture was filtered and subjected to chromatography on a silica gel column with an eluent system of n-hexa... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Carboxylic acid | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | C(Cl)Cl | null | 4 | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCCCCCCCCCCCBr>C(Cl)Cl>O=C(O)C=CCCCCCCCCCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8d8a1979a6ba45fc9223a71b0005d2f2 | O=C(O)C=CCCCCCCCCCCCF>>O=C(O)CCCCCCCCCCCCCF | Cl.FCCCCCCCCCCCC=CC(=O)O>>FCCCCCCCCCCCCCC(=O)O | [O:1]=[C:2]([OH:3])[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][F:17]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][F:17] | O=C(O)C=CCCCCCCCCCCCF | O=C(O)CCCCCCCCCCCCCF | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | null | [C:1]-[C:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | 75.1 | [{"value": 75.1, "product": "FCCCCCCCCCCCCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | The methyl ester of 14-fluoro-2-tetradecenoic acid (3.3 g) was dissolved in methanol (20 ml), in which 10% palladium/carbon (0.9 g) was suspended, and a 10% methanolic hydrochloric acid solution (2 ml) was added. The mixture was stirred under hydrogen atmosphere for 12 hours. The reaction mixture was filtered, and a la... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | [Pd].CO | null | 12 | O=C(O)C=CCCCCCCCCCCCF>[Pd].CO>O=C(O)CCCCCCCCCCCCCF |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e8fed5ab88ed4c3f9c61dbe025a9c243 | CCCCCCCCCCCCC(Br)C(=O)O.[Cl-]>>CCCCCCCCCCCCC(Cl)C(=O)O | BrC(C(=O)O)CCCCCCCCCCCC.[Cl-].[Ca+2].[Cl-].C(C)N(CC)CC>>ClC(C(=O)O)CCCCCCCCCCCC | Br[CH:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:15](=[O:16])[OH:17].[Cl-:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([Cl:14])[C:15](=[O:16])[OH:17] | CCCCCCCCCCCCC(Br)C(=O)O.[Cl-] | CCCCCCCCCCCCC(Cl)C(=O)O | null | [Cl-].C(C)[N+](CC)(CC)CC | C(C)#N | Functional Group Interconversion | OtherReaction | fc4c95ec611a23fa9eb0d0b34d24ddfd0af4934017bf7e16055623ff186b1c70 | 9c89c0272f12ed506fa41afbecb80fab32cea2e763e86c5c1186abbe8b274cb0 | null | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[Cl-;H0;D0:7]>>[C:3]-[C:2]-[CH;D3;+0:1](-[Cl;H0;D1;+0:7])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 75.4 | [{"value": 75.4, "product": "ClC(C(=O)O)CCCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | To 2-bromotetradecanoic acid (2 g) dissolved in acetonitrile (100 ml) were added calcium chloride (7.2 g), tetraethylammonium chloride (2.2 g) and triethylamine (0.84 ml), and the mixture was stirred at 80° C. for 3 hours. After precipitates produced by cooling the reaction mixture was removed by filtration, the filtra... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | Secondary halide | null | null | null | Br- | [Cl-].C(C)[N+](CC)(CC)CC.C(C)#N | 80 | 3 | CCCCCCCCCCCCC(Br)C(=O)O.[Cl-]>[Cl-].C(C)[N+](CC)(CC)CC.C(C)#N>CCCCCCCCCCCCC(Cl)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a2b3187b071449d8bca18e6b39088d1e | CCCCCCCCCCCC(OC(=S)C(=O)c1ncc[nH]1)C(F)(F)C(=O)OCC>>CCCCCCCCCCCCC(F)(F)C(=O)OCC | FC(C(=O)OCC)(C(CCCCCCCCCCC)OC(=S)C(=O)C=1NC=CN1)F.C(CCC)[SnH](CCCC)CCCC>>FC(C(=O)OCC)(CCCCCCCCCCCC)F | O=C(C(=S)O[CH:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:13]([F:14])([F:15])[C:16](=[O:17])[O:18][CH2:19][CH3:20])c1ncc[nH]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([F:14])([F:15])[C:16](=[O:17])[O:18][CH2:19][CH3:20] | CCCCCCCCCCCC(OC(=S)C(=O)c1ncc[nH]1)C(F)(F)C(=O)OCC | CCCCCCCCCCCCC(F)(F)C(=O)OCC | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | 33e0b9ffc5e9d9f283c01a872add6bc600ed038dd2732f41b3fa615c564ee12a | aa7a08c3d7af5bdeb14789f7ec025f56e9c6ecadad2d92f21d75c2abe4e540eb | null | O=C(-C(=S)-O-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-c1:[nH]:c:c:n:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 77.5 | [{"value": 77.5, "product": "FC(C(=O)OCC)(CCCCCCCCCCCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl bromodifluoroacetate (6.0 g) and dodecyl aldehyde (1.84 g) were mixed with anhydrous tetrahydrofuran (40 ml) under argon atmosphere, and the solution was added dropwise to a suspension of zinc powder (2.2 g) and copper bromide (I) (0.22 g) in anhydrous tetrahydrofuran (40 ml) which was heated to a refluxing tempe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Thiocarbonyl | null | c1c[nH]cn1 | null | null | Other | C1(=CC=CC=C1)C | null | null | CCCCCCCCCCCC(OC(=S)C(=O)c1ncc[nH]1)C(F)(F)C(=O)OCC>C1(=CC=CC=C1)C>CCCCCCCCCCCCC(F)(F)C(=O)OCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9d416a2f1a044ab1a2c621a9ec932054 | CCCCCCCCCCCCCC(OC(=S)C(=O)c1ncc[nH]1)C(F)(F)C(=O)OCC>>CCCCCCCCCCCCCCC(F)(F)C(=O)OCC | FC(C(=O)OCC)(C(CCCCCCCCCCCCC)OC(=S)C(=O)C=1NC=CN1)F.C(CCC)[SnH](CCCC)CCCC>>FC(C(=O)OCC)(CCCCCCCCCCCCCC)F | O=C(C(=S)O[CH:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:15]([F:16])([F:17])[C:18](=[O:19])[O:20][CH2:21][CH3:22])c1ncc[nH]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([F:16])([F:17])[C:18](=[... | CCCCCCCCCCCCCC(OC(=S)C(=O)c1ncc[nH]1)C(F)(F)C(=O)OCC | CCCCCCCCCCCCCCC(F)(F)C(=O)OCC | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | 33e0b9ffc5e9d9f283c01a872add6bc600ed038dd2732f41b3fa615c564ee12a | aa7a08c3d7af5bdeb14789f7ec025f56e9c6ecadad2d92f21d75c2abe4e540eb | null | O=C(-C(=S)-O-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-c1:[nH]:c:c:n:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 87.8 | [{"value": 87.8, "product": "FC(C(=O)OCC)(CCCCCCCCCCCCCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl bromodifluoroacetate (11.2 g) and tetradecyl aldehyde (3.96 g) were mixed with anhydrous tetrahydrofuran (80 ml) under argon atmosphere, and the solution was added dropwise to a suspension of zinc powder (4.1 g) and copper bromide (I) (0.41 g) in anhydrous tetrahydrofuran (80 ml) which was heated to a refluxing t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Thiocarbonyl | null | c1c[nH]cn1 | null | null | Other | C1(=CC=CC=C1)C | null | null | CCCCCCCCCCCCCC(OC(=S)C(=O)c1ncc[nH]1)C(F)(F)C(=O)OCC>C1(=CC=CC=C1)C>CCCCCCCCCCCCCCC(F)(F)C(=O)OCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0abced53d7184404b9c36cc1a42ea206 | CCCCCCCCCCCCCC[C@H](OC(C)=O)C(=O)O>>CCCCCCCCCCCCCC[C@H](O)C(=O)O | C(C)(=O)O[C@H](C(=O)O)CCCCCCCCCCCCCC>>O[C@H](C(=O)O)CCCCCCCCCCCCCC | CC(=O)[O:16][C@@H:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:17](=[O:18])[OH:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]([OH:16])[C:17](=[O:18])[OH:19] | CCCCCCCCCCCCCC[C@H](OC(C)=O)C(=O)O | CCCCCCCCCCCCCC[C@H](O)C(=O)O | null | null | [OH-].[K+].C(C)O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | null | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | 70 | CELSIUS | 2 | HOUR | (S)-(+)-2-Acetoxyhexadecanoic acid (0.5 g; prepared by the method described in Agric. Biol. Chem., 54(12), 3337-3338, 1990) was dissolved in a solution of potassium hydroxide (1.0 g) in 50% aqueous ethanol was stirred at 70° C. for 2 hours. After the ethanol was evaporated, the reaction mixture was acidified with citri... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | null | HO- | [OH-].[K+].C(C)O | 70 | 2 | CCCCCCCCCCCCCC[C@H](OC(C)=O)C(=O)O>[OH-].[K+].C(C)O>CCCCCCCCCCCCCC[C@H](O)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f6e92fbde84048c09814171d21d10dad | CCCCCCCCCCC(Br)C(=O)O.Oc1ccccc1>>CCCCCCCCCCC(Oc1ccccc1)C(=O)O | BrC(C(=O)O)CCCCCCCCCC.[H-].[Na+].C1(=CC=CC=C1)O>>O(C1=CC=CC=C1)C(C(=O)O)CCCCCCCCCC | Br[CH:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:19](=[O:20])[OH:21].[OH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:19](=[O:20])[OH:21] | CCCCCCCCCCC(Br)C(=O)O.Oc1ccccc1 | CCCCCCCCCCC(Oc1ccccc1)C(=O)O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccccc1 | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:3]-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 92 | [{"value": 92.0, "product": "O(C1=CC=CC=C1)C(C(=O)O)CCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | To 2-bromododecanoic acid (500 mg) dissolved in N,N-dimethylformamide (DMF, 10 ml) at 0° C. were added 60% sodium hydride (163 mg) followed by phenol (154 mg), and the mixture was stirred for 17 hours. Then, the solvent (DMF) was evaporated, and the residue was distributed into water and ethyl acetate. The ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C=O)C | null | 17 | CCCCCCCCCCC(Br)C(=O)O.Oc1ccccc1>CN(C=O)C>CCCCCCCCCCC(Oc1ccccc1)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-dc260564c78b4333bf5d34d254210f46 | CC(=O)OC(C)=O.CCCCCCCCCCCCCC[C@@H](O)C(=O)O>>CCCCCCCCCCCCCC[C@@H](OC(C)=O)C(=O)O | O.O[C@@H](C(=O)O)CCCCCCCCCCCCCC.C(C)(=O)OC(C)=O.C(C)(=O)OCC>>C(C)(=O)O[C@@H](C(=O)O)CCCCCCCCCCCCCC | CC(=O)O[C:17]([CH3:18])=[O:19].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]([OH:16])[C:20](=[O:21])[OH:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]([O:16][C:17]([CH3:18])=[O:19])[... | CC(=O)OC(C)=O.CCCCCCCCCCCCCC[C@@H](O)C(=O)O | CCCCCCCCCCCCCC[C@@H](OC(C)=O)C(=O)O | null | null | N1=CC=CC=C1 | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | null | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | null | null | 12 | HOUR | To (R)-(+)-2-hydroxyhexadecanoic acid (0.5 g; prepared according to the method described in Agric. Biol. Chem., 54(12), 3337-3338, 1990) dissolved in pyridine (15 ml) was added acetic anhydride (0.23 ml) at 0° C., and the mixture was stirred 12 hours. The reaction mixture was distributed into ethyl acetate and water, a... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | null | HO- | N1=CC=CC=C1 | null | 12 | CC(=O)OC(C)=O.CCCCCCCCCCCCCC[C@@H](O)C(=O)O>N1=CC=CC=C1>CCCCCCCCCCCCCC[C@@H](OC(C)=O)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ca71c87a03d64cd390099a392040b011 | CCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCCCCC/C=C/C=C/C(=O)O | CCCCCC.C(C)(=O)OCC.C(\C=C\CCCCCCCCC)=O.C(=O)(OC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(\C=C\C=C\CCCCCCCCC)(=O)O | O=[CH:12]/[CH:11]=[CH:10]/[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].C[O:16][C:14]([CH:13]=P(c1ccccc1)(c1ccccc1)c1ccccc1)=[O:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14](=[O:15])[OH:16] | CCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCCCCC/C=C/C=C/C(=O)O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 6b3c0eb3ed6d44a9f973c5f4266e84250e8ebf5a1d1e0860ef8cdbe9a0241cc8 | 0aab88bc004204544a4ed5a027815bc5384a304c50cca0b067c18dd1842afcf6 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:5]/[C:6]=[C:7]/[C:8]-[C:9]>>[C:9]-[C:8]/[C:7]=[C:6]/[CH;D2;+0:5]=[CH;D2;+0:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 2 | HOUR | To a solution of trans-2-dodecenal (4.5 g) dissolved in methylene chloride (80 ml) was added (carbomethoxymethylene)triphenylphosphorane (8.3 g), and the mixture was stirred for 2 hours. The reaction mixture was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Carboxylic acid.Conjugated diene | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | C(Cl)Cl | null | 2 | CCCCCCCCC/C=C/C=O.COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)Cl>CCCCCCCCC/C=C/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3ded1444f73f4a6696dd39717f760029 | CCCCCCCCCC=CC=CC(=O)O>>CCCCCCCCC/C=C/C=C/C(=O)O | C(C=CC=CCCCCCCCCC)(=O)O.[N+](=O)([O-])C1=CC=C(C=C1)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(\C=C\C=C\CCCCCCCCC)(=O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][CH:12]=[CH:13][C:14](=[O:15])[OH:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14](=[O:15])[OH:16] | CCCCCCCCCC=CC=CC(=O)O | CCCCCCCCC/C=C/C=C/C(=O)O | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 12 | HOUR | To a solution of trans-2-dodecenal (4.5 g) dissolved in methylene chloride (80 ml) was added (carbomethoxymethylene)triphenylphosphorane (8.3 g), and the mixture was stirred for 2 hours. The reaction mixture was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CN(C=O)C | null | 12 | CCCCCCCCCC=CC=CC(=O)O>CN(C=O)C>CCCCCCCCC/C=C/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e8eca68b93434d91b88866b0bebf0aa6 | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1>>O=C1CCC(c2ccc(Cl)cc2)=NN1 | ClC1=CC=C(C(=O)CCC(=O)O)C=C1.O.NN>>ClC1=CC=C(C=C1)C=1CCC(NN1)=O | [NH2:13][NH2:14].O=[C:5]([CH2:4][CH2:3][C:2](O)=[O:1])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)=[N:13][NH:14]1 | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1 | O=C1CCC(c2ccc(Cl)cc2)=NN1 | null | null | C(C)O | Acylation | OtherReaction | 16e715242dd5e92f711d46176c552652cef6c6f4fed9bc9a09a311d5b0b86cea | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[NH2;D1;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])=[N;H0;D2;+0:9]-[NH;D2;+0:10]-1 | 81.5 | [{"value": 80.0, "product": "ClC1=CC=C(C=C1)C=1CCC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.5, "product": "ClC1=CC=C(C=C1)C=1CCC(NN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-(4-chlorobenzoyl)propionic acid (20 g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=NNCCC1 | C1=NNCCC1.c1ccccc1 | HO- | C(C)O | null | null | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1>C(C)O>O=C1CCC(c2ccc(Cl)cc2)=NN1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d57caf1a17ad4900ae77169a0f4ca2c5 | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.CC(C)(C)NN>>CC(C)(C)N1N=C(c2ccc(Cl)cc2)CCC1=O | ClC1=CC=C(C(=O)C(C(=O)O)C)C=C1.C(C)(=O)[O-].[Na+].Cl.C(C)(C)(C)NN>>ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O | O=[C:7]([c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[CH:15]([CH3:16])[C:17](O)=[O:18].[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][NH2:6]>>[CH3:1][C:2]([CH3:3])([CH3:4])[N:5]1[N:6]=[C:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[CH2:15][CH2:16][C:17]1=[O:18] | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.CC(C)(C)NN | CC(C)(C)N1N=C(c2ccc(Cl)cc2)CCC1=O | null | null | C(CCC)O | Acylation | OtherReaction | 4e477d09c29dc9649665c2a512a7ab66ed0db9837b745e511eba3c76a3cc18d7 | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[CH3;D1;+0:4])-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2;+0:13]-[NH2;D1;+0:14]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[N;H0;D3;+0:13]1-[N;H0;D2;+0:14]=[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-[CH2;D2;+0:3]-[CH2;D2;+... | 34.4 | [{"value": 34.4, "product": "ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chlorobenzoylpropionic acid (4.24 g) in n-butanol (150 ml) was added anhydrous sodium acetate (1.54 g) and t-butylhydrazine hydrochloride (2.75 g) portionwise at room temperature. The resulting mixture was refluxed for 9 hours distilling off 65 ml of n-butanol during that time. The resulting mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=N[NH]CCC1 | C1=N[NH]CCC1.c1ccccc1 | HO- | C(CCC)O | null | null | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.CC(C)(C)NN>C(CCC)O>CC(C)(C)N1N=C(c2ccc(Cl)cc2)CCC1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ab0ba8700c0046f09a63221f9ccb7040 | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>>O=C(O)CCC(=O)c1cccc(Cl)c1 | C(CCC(=O)OC)(=O)OC.[Na].C(C)O.ClC=1C=C(C(=O)OC)C=CC1.C(CCC(=O)OC)(=O)OC>>ClC=1C=C(C(=O)CCC(=O)O)C=CC1 | COC(=O)[CH2:5][CH2:4][C:2](=[O:1])[O:3]C.CO[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1 | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | null | null | CCOCC | C-C Coupling | OtherReaction | 6d482de2a0c1fffe47581cf2d6dc0eefca79628574252eec326be9292f335afe | 1f69704fe402a3eb0e91a243a59f68f972592be61b4c787368515903d4c85726 | c1ccccc1 | C-O-C(=O)-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C.C-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]>>[O;D1;H0:4]=[C:3](-[OH;D1;+0:5])-[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | Sodium (11 g, spheres) was added to 200 ml ethanol with stirring. When the gas evolution ceased, methyl 3-chlorobenzoate (10 g, 0.057 mole) and dimethyl succinate (9.0 g, 0.615 mole) were added rapidly and the mixture was stirred for 5 minutes at room temperature. The mixture was slowly concentrated on a rotary evapora... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Carboxylic acid.Ketone | null | null | c1ccccc1 | HO- | CCOCC | null | null | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>CCOCC>O=C(O)CCC(=O)c1cccc(Cl)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cedee21867a145598085b81b020f6c0c | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl>>Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl | CC1=CC=C(C(=O)CCC(=O)O)C=C1.[Cl-].[Al+3].[Cl-].[Cl-].ClCl>>ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl | [CH3:1][c:2]1[cH:3][cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][cH:15]1.[Cl:4][Cl:16]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][c:15]1[Cl:16] | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl | Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | d2a751fe92dcfde720edd5e4971c1aa6cc149bff4a6d230cc6b5cac59ec9498c | 861258def4b3bd7367f8a87cde43fe585d40dc3669ea29055dbcb9a2de101a4d | c1ccccc1 | [C;D1;H3:1]-[c:2]1:[cH;D2;+0:3]:[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[cH;D2;+0:9]:1.[Cl;H0;D1;+0:10]-[Cl;H0;D1;+0:11]>>[C;D1;H3:1]-[c:2]1:[c;H0;D3;+0:3](-[Cl;H0;D1;+0:10]):[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9]:1-[Cl;H0;D1;+0:11] | 44.2 | [{"value": 44.2, "product": "ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 3-(4-methylbenzoyl)propionic acid (7.5 g) and methylene chloride (250 ml) was added slowly portionwise aluminum chloride (15 g) at 0° C. After the addition was completed chlorine gas was bubbled in slowly at 0° C. After 6 hours the reaction mixture was poured into a mixture of hydrochloric acid and ice ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide.Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C(Cl)Cl | null | null | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl>C(Cl)Cl>Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fdc4f689f70b4f6e8ca09c1cf4b89413 | C1=COCCC1.OCC#CCO>>OCC#CCOC1CCCCO1 | C(C#CCO)O.O1CCCC=C1>>O1C(CCCC1)OCC#CCO | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[OH:1][CH2:2][C:3]#[C:4][CH2:5][OH:6]>>[OH:1][CH2:2][C:3]#[C:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1 | C1=COCCC1.OCC#CCO | OCC#CCOC1CCCCO1 | null | C1(=CC=C(C=C1)S(=O)(=O)O)C | CCOCC | Heteroatom Alkylation and Arylation | oxa-Michael addition | abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f | c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a | C1CCOCC1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8]#[C:9]-[C:10]-[OH;D1;+0:11]>>[C:7]-[C:8]#[C:9]-[C:10]-[O;H0;D2;+0:11]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | 68.8 | [{"value": 68.8, "product": "O1C(CCCC1)OCC#CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of wate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | C1(=CC=C(C=C1)S(=O)(=O)O)C.CCOCC | null | null | C1=COCCC1.OCC#CCO>C1(=CC=C(C=C1)S(=O)(=O)O)C.CCOCC>OCC#CCOC1CCCCO1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-da4529aba9db4f9fbccbd6f49776aef3 | C#CC1CCCCC1.C=O>>OCC#CC1CCCCC1 | C1(CCCCC1)C#C.C=O.C=O>>C1(CCCCC1)C#CCO | [CH:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.[O:1]=[CH2:2]>>[OH:1][CH2:2][C:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | C#CC1CCCCC1.C=O | OCC#CC1CCCCC1 | null | null | CCOCC | C-C Coupling | OtherReaction | b068d8bba9f864ba971dd324292d9b3526f0235b4ab7e3a9ce6aa76a39c4a1e7 | 22ebec2cc94dd24863aea8793d450cfe0691e1036be204d1a4c79c16effe90a4 | C1CCCCC1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[C:4]#[CH;D1;+0:5]>>[C:3]-[C:4]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | To a solution of ethyl magesium bromide (prepared from 2.5 g of magnesium turning and 11.3 g of bromoethane) in ether was added dropwise a solution of 10.2 g of cyclohexylacetylene in ether and the reaction mixture was refluxed for 2 hours. The reaction mixture was cooled to ambient temperature and anhydrous formaldehy... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Alkyne | Primary alcohol.Alkyne | null | null | C1CCCCC1 | null | CCOCC | null | null | C#CC1CCCCC1.C=O>CCOCC>OCC#CC1CCCCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-45b75568609e419ea4cfd515f83bcfca | O=C1CCC(c2ccc(Cl)cc2)=NN1>>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1CCC(NN1)=O.C(C)(=O)O.BrBr>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=O | [O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)=[N:13][NH:14]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=C1CCC(c2ccc(Cl)cc2)=NN1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 73c80fbcc9dd7a9125aaf1059d9d4eab31b342d21fc860abf5e65fd78456864b | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1ccc(-c2ccccc2)n[nH]1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])=[N;H0;D2;+0:11]-[NH;D2;+0:12]-1>>[O;D1;H0:1]=[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[n;H0;D2;+0:11]:[nH;D2;+0:12]:1 | 93.1 | [{"value": 89.0, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | C1=NNCCC1 | c1cccnn1 | c1cccnn1.c1ccccc1 | null | O | null | null | O=C1CCC(c2ccc(Cl)cc2)=NN1>O>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-797668b8c0f44afbb749e8e72c50c607 | FC1(F)CC(Cl)(Cl)C1(F)Cl>>FC1(F)C=C(Cl)C1(F)Cl | ClC1(C(C(C1)(F)F)(F)Cl)Cl.O.Cl>>ClC1(C(C=C1Cl)(F)F)F | Cl[C:5]1([Cl:6])[CH2:4][C:2]([F:1])([F:3])[C:7]1([F:8])[Cl:9]>>[F:1][C:2]1([F:3])[CH:4]=[C:5]([Cl:6])[C:7]1([F:8])[Cl:9] | FC1(F)CC(Cl)(Cl)C1(F)Cl | FC1(F)C=C(Cl)C1(F)Cl | null | null | CCOCC.C(C)N(CC)CC | Functional Group Interconversion | OtherReaction | 0ca523bc88d44f4371960ac2ff9ed0bbb8882337b7061f7fba5b4787f1e02481 | 986b135105e7920109b424799136a4a8281fb4a0f49253ce1bf5d4426ed78637 | C1=CCC1 | Cl-[C;H0;D4;+0:1]1(-[Cl;D1;H0:2])-[CH2;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1]1=[CH;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9] | 79 | [{"value": 79.0, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ethe... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | Alkenyl halide | C1CCC1 | C1=CCC1 | C1=CCC1 | HCl | CCOCC.C(C)N(CC)CC | null | 8 | FC1(F)CC(Cl)(Cl)C1(F)Cl>CCOCC.C(C)N(CC)CC>FC1(F)C=C(Cl)C1(F)Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c6372a9c73d245e185b295d5560afbcd | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>>O=C(O)C(F)C(F)(F)C(=O)O | ClC(C(C(=O)O)(F)F)(C(=O)O)F>>FC(C(=O)O)(C(C(=O)O)F)F | Cl[C:6]([C:4]([C:2](=[O:1])[OH:3])([F:5])[F:7])([F:8])[C:9](=[O:10])[OH:11]>>[O:1]=[C:2]([OH:3])[CH:4]([F:5])[C:6]([F:7])([F:8])[C:9](=[O:10])[OH:11] | O=C(O)C(F)(F)C(F)(Cl)C(=O)O | O=C(O)C(F)C(F)(F)C(=O)O | null | [Zn] | O1CCOCC1 | Functional Group Addition | Dehalogenation | 7f145230bfb0115349e969b2f2fa1359cfafe8c166e52b50a867192005e1f5bc | d6722b0df465660a9eeeaca5a8f5b3dbb2d1ebccb44917f2eca97a85bf850d06 | null | Cl-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;H0;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[F;D1;H0:7]-[CH;D3;+0:6](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;H0;D1;+0:8])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 40.7 | [{"value": 32.0, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Tertiary halide.Tertiary halide.Secondary halide | null | null | null | Other | [Zn].O1CCOCC1 | null | 10 | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>[Zn].O1CCOCC1>O=C(O)C(F)C(F)(F)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3dd83745b9af4134b4460fbd5e19d89c | O=C1CCC(=O)O1.c1ccc2ccccc2c1>>O=C(O)CCC(=O)c1cccc2ccccc12 | Cl.[Cl-].[Cl-].[Cl-].[Al+3].C1=CC=CC2=CC=CC=C12.C1(CCC(=O)O1)=O>>C1(=CC=CC2=CC=CC=C12)C(=O)CCC(=O)O | [O:1]=[C:2]1[O:3][C:6](=[O:7])[CH2:5][CH2:4]1.[cH:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | O=C1CCC(=O)O1.c1ccc2ccccc2c1 | O=C(O)CCC(=O)c1cccc2ccccc12 | null | null | [N+](=O)([O-])C1=CC=CC=C1 | C-C Coupling | OtherReaction | d1b47ca78c3ceb45955ddf79d2b2d22c1a0978cf9fa8ded4c5ee0a8331deac4e | 4836357c99dfeeac9d5083fedc379181a858ae45ac77bd85eb46e7e1a9df36f0 | c1ccc2ccccc2c1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11](:[c:12]):[c:13]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | A mixture of naphthalene (40 g) and succinic anhydride (20 g) was added to a well stirred suspension of aluminum trichloride (55 g) in nitrobenzene (140 ml). The resulting mixture was stirred overnight at room temperature. The mixture was then poured slowly onto ice-water (600 g) and acidified with 6N-hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid.Ketone | C1CCOC1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | null | [N+](=O)([O-])C1=CC=CC=C1 | null | null | O=C1CCC(=O)O1.c1ccc2ccccc2c1>[N+](=O)([O-])C1=CC=CC=C1>O=C(O)CCC(=O)c1cccc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7e76d25660ad40c085f499c321d7583b | NN.O=C(O)CCCC(=O)c1ccccc1>>O=c1cccc(-c2ccccc2)nn1 | C(C1=CC=CC=C1)(=O)CCCC(=O)O.NN.O>>C1(=CC=CC=C1)C1=CC=CC(N=N1)=O | [NH2:13][NH2:14].O=[C:6]([CH2:5][CH2:4][CH2:3][C:2](O)=[O:1])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[O:1]=[c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][n:14]1 | NN.O=C(O)CCCC(=O)c1ccccc1 | O=c1cccc(-c2ccccc2)nn1 | null | null | CCOCC.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | a31553d36b14882561a6dcdd04ef456bc0e14ea189c472490f94f02ebbe3ca3f | eadf9e657b4bde18ed656e299092aac7dd81eee1face1030775c3edd6ccba31c | O=c1cccc(-c2ccccc2)nn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[NH2;D1;+0:12]-[NH2;D1;+0:13]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:12]:[n;H0;D2;+0... | 39 | [{"value": 39.0, "product": "C1(=CC=CC=C1)C1=CC=CC(N=N1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 10 g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washe... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | null | null | c1cccc[nH]n1 | c1cccc[nH]n1.c1ccccc1 | HO- | CCOCC.C1(=CC=CC=C1)C | null | null | NN.O=C(O)CCCC(=O)c1ccccc1>CCOCC.C1(=CC=CC=C1)C>O=c1cccc(-c2ccccc2)nn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9860c66498764eb09bfdddf86dbf0973 | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>>COC(=O)C1Cc2cc(Cl)ccc2C1=O | COC(OC)=O.[H-].[Na+].ClC=1C=C2CCC(C2=CC1)=O.[H][H]>>C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O | CO[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15] | COC(=O)OC.O=C1CCc2cc(Cl)ccc21 | COC(=O)C1Cc2cc(Cl)ccc2C1=O | null | null | C(OC)COC | C-C Coupling | OtherReaction | c2c31337dfb867d8c28bc65df0ad4496f817a712a58e176523b47d7fdb6e4f91 | d76b6fc9d01d8258e5777a3b2326a8d78a9d9a55717b27736ba55600205f4ed0 | O=C1CCc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[c:9]:[c:10]-[C:6]-1=[O;D1;H0:5] | 45 | [{"value": 45.0, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ketone.Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | C(OC)COC | 60 | null | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>C(OC)COC>COC(=O)C1Cc2cc(Cl)ccc2C1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5f1ff2ddc3ca4af48574de1849438805 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>>CN(C)C=C(C=O)c1ccc(Cl)cc1 | CN(C)C=O.P(=O)(Cl)(Cl)Cl.ClC1=CC=C(C=C1)CC(=O)O.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC=C(C=C1)C(C=O)=CN(C)C | O=[CH:4][N:2]([CH3:1])[CH3:3].O=[C:6]([CH2:5][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[OH:7]>>[CH3:1][N:2]([CH3:3])[CH:4]=[C:5]([CH:6]=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1 | CN(C)C=C(C=O)c1ccc(Cl)cc1 | null | null | null | Acylation | OtherReaction | cbf378fe57a2b8d8304e623fb5ce9ee6fb9f6e90d9c6f965226d56b103180e6d | a9c635686380f13b6b5c45d80d4aef36b30fdab0aef140b81f04c277f7ba737d | c1ccccc1 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6].O=[CH;D2;+0:7]-[#7:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[#7:8](-[C;D1;H3:10])-[CH;D2;+0:7]=[C;H0;D3;+0:3](-[CH;D2;+0:1]=[O;H0;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 8 | HOUR | Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide | Enamine.Aldehyde | null | null | c1ccccc1 | HO- | null | null | 8 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>>CN(C)C=C(C=O)c1ccc(Cl)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8a27099ba3e54638acb71dd1e6d15789 | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | C(C)(=O)O.ClC1=CC=C(C=C1)C(C=O)=CN(C)C.C[O-].[Na+].C(#N)CC(=O)N>>C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O | CN(C)[CH:13]=[C:5]([CH:4]=O)[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.[N:1]#[C:2][CH2:3][C:15]([NH2:14])=[O:16]>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14][c:15]1=[O:16] | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | 4fb69599b2ad512416349de44ee025f314a8ccdb2c8ad729cdf94ea75cf3109a | 46cf335065eccd013987994a3f086665eb273ac87eb3153099a47e61dd329581 | O=c1ccc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[N;D1;H0:9]#[C:10]-[CH2;D2;+0:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[O;D1;H0:14]>>[N;D1;H0:9]#[C:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:1]:[nH;D2;+0:13]:[c;H0;D3;+0... | null | [] | null | null | null | null | To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic acid (50 m... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Primary amide | null | null | c1cnccc1 | c1cnccc1.c1ccccc1 | HO- | O.CO | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>O.CO>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e8a7db5bb45348e4825027ea85a44aeb | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=C1)C=1C=CC(NC1)=O | N#C[c:3]1[c:2](=[O:1])[nH:14][cH:13][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:4]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | null | null | OP(=O)(O)O | Miscellaneous | OtherReaction | 145adc421652def73603eb299eace1e2e3a197522b719b6949c0145a4308d11b | 4f08c5adfb6d80fba1093598fc51ce38f180c76537f67052d397b642cb6f3b89 | O=c1ccc(-c2ccccc2)c[nH]1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1=[O;D1;H0:7]>>[O;D1;H0:7]=[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1 | 75.6 | [{"value": 75.6, "product": "ClC1=CC=C(C=C1)C=1C=CC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-cyano-5-(4-chlorophenyl)-2-pyridinone (4.6 g) and 85% H3PO4 (60 ml) was heated at reflux for 16 hours. The resulting mixture was cooled to room temperature, poured into ice/water and filtered yielding 3.1 g of 5-(4-chlorophenyl)-2-pyridinone as a yellow solid.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | c1cnccc1 | c1cccnc1 | c1cccnc1.c1ccccc1 | Other | OP(=O)(O)O | null | null | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>OP(=O)(O)O>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4a5e6f7635a544fd8a7da7e5a21ae34c | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | [Cl-].[NH4+].[H-].[Na+].N1C(C=CC=C1)=O.CCCCCC.C(C)(=O)OCC.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=CC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[CH2:9]([CH3:10])[CH2:15][CH2:14][CH2:12][CH3:11].[nH:6]1[cH:7][cH:8][cH:16][cH:17][c:18]1=[O:19].[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][cH:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-] | CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | c16e53991381708a0d74f5092b5e25b0353184189763eaae006dd565c1174ab9 | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ccc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH3;D1;+0:10].[Cl-;H0;D0:11].[O;D1;H0:12]=[c:13]1:[c:14]:[c:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:6]2:[cH;D2;+0:5]:[cH;D2;+0:... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 200 mg) in dry DMF (50 ml) at 0° C. was added the preceding pyridinone and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne dropwise. The resulting mixture was kept at 0° C. during one half hour and poured into satura... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b6cd7a1a7deb4b5c82a7d80a16457725 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1>>O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | C(C)(=O)OCC.ClC1=CC=C(N)C=C1.N1=CC=CC=C1.C(C=CC1=CC=CC=C1)(=O)Cl>>ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.Cl[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | null | null | O.C1(=CC=CC=C1)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(C=Cc1ccccc1)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]=[C:4]-[c:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | 0 | CELSIUS | 15 | MINUTE | To a mixture of 4-chloroaniline (16.2 g), toluene (120 ml), and pyridine (11 ml) at 0° C., cinnamoyl chloride (20.0 g) in 120 ml of toluene was added dropwise. After stirring 15 minutes at 0° C. the reaction mixture was poured into a mixture of ethyl acetate: water (250 ml:250 ml). The organic layer was separated and e... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | O.C1(=CC=CC=C1)C | 0 | 0.25 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1>O.C1(=CC=CC=C1)C>O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-caeb36afcb1a4a7a81c6fa5431263e1b | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>>O=c1ccc2c(Cl)cccc2[nH]1 | ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O.[Cl-].[Al+3].[Cl-].[Cl-]>>ClC1=C2C=CC(NC2=CC=C1)=O | c1ccc([CH:4]=[CH:3][C:2](=[O:1])[NH:12][c:11]2[cH:5][cH:8][c:6]([Cl:7])[cH:9][cH:10]2)cc1>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]2[nH:12]1 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | O=c1ccc2c(Cl)cccc2[nH]1 | null | null | ClC1=CC=CC=C1 | Reduction | OtherReaction | ebe7e954f82f1e726cf9b7a8863216fec31733c3d8bfbb1cc71c49312cec65ac | 10d6d5b071f1d84b20b253ce9eadaed211c373c6ee607356078792f13319351a | O=c1ccc2ccccc2[nH]1 | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-c2:c:c:c:c:c:2):[c:11]:[cH;D2;+0:12]:1>>[Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:12]:[c:11]:[c:5]2:[nH;D2;+0:6]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:[c;H0;D3;+... | null | [] | 125 | CELSIUS | 3 | HOUR | To a mixture of N-(4-chlorophenyl)cinnamamide (8.3 g), and chlorobenzene (60 ml) was added portionwise aluminum chloride (21.4 g) under nitrogen at room temperature and the reaction mixture was slowly warmed up to 125° C. and kept at that temperature for 3 hours. The reaction mixture was cooled down and poured over 400... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccc2ccccc2n1 | c1ccc2ccccc2n1 | Other | ClC1=CC=CC=C1 | 125 | 3 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>ClC1=CC=CC=C1>O=c1ccc2c(Cl)cccc2[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8496c7d9967a467b8295a965a76f92d9 | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>>CCC#CCn1c(=O)ccc2c(Cl)cccc21 | [Cl-].[NH4+].N1C(C=CC2=CC=CC=C12)=O.[H-].[Na+].BrCC#CCC>>ClC1=C2C=CC(N(C2=CC=C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[nH:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[cH:12][cH:14][cH:15][cH:16][c:17]12.[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12 | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-] | CCC#CCn1c(=O)ccc2c(Cl)cccc21 | null | null | CCCCCC.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a61336fe7a89ec0981a525297b55629e44e830f13f91df56a44bf01390d8c69d | dbda6588fa29cbbc0e3c3f601e69924b300990bdcc56b8cec0535d1258039346 | O=c1ccc2ccccc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[Cl-;H0;D0:5].[O;D1;H0:6]=[c:7]1:[c:8]:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:12]:[c:13]:[c:14]:[c:15]:2:[nH;D2;+0:16]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:16]1:[c:15]2:[c:14]:[c:13]:[c:12]:[c;H0;D3;+0:11](-[Cl;H0;D1;+0:5]):[c:10]:2:[c:9]:[c:8]:[c:7]:1=[O;D1;H0:6] | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and po... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccc2ccccc2n1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | CCCCCC.CN(C)C=O | 0 | null | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>CCCCCC.CN(C)C=O>CCC#CCn1c(=O)ccc2c(Cl)cccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aec5b1ee340c4936804d6f5ce99e56a8 | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | [Cl-].[NH4+].ClC1=CC=C(C=C1)C(C=O)=CN(C)C.NC(=O)N.Cl>>ClC1=CC=C(C=C1)C=1C=NC(NC1)=O | CN(C)[CH:4]=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH:13]=O.[O:1]=[C:2]([NH2:3])[NH2:14]>>[O:1]=[c:2]1[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O | O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | null | null | O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 0e1bb7c6fc2fa2fbd0239b648ae136ef123b13ddeb9947c50b8f38d453d7d183 | 55a949c5abf218b0e7fd0015b81e86fb975fa441e5ac6bd395c3346bb38599f7 | O=c1ncc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[O;D1;H0:12]>>[O;D1;H0:12]=[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:3]:[nH;D2;+0:9]:1 | 29.7 | [{"value": 29.7, "product": "ClC1=CC=C(C=C1)C=1C=NC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Urea | null | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | O.C(C)O | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>O.C(C)O>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-db58505f9b834696a016840ee24d2c3b | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | [Cl-].[NH4+].CCCCCC.[H-].[Na+].N1C(C=CC=C1)=O.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=NC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].C[CH2:15][CH2:14][CH2:12][CH2:11][CH3:10].[nH:6]1[cH:7][cH:8][cH:16][cH:9][c:18]1=[O:19].[Cl-:13].[NH4+:17]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][n:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+] | CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | b4467fdd65493649554b053844b88f7aedac75ecb5e83a2819a9163270cc6b1f | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ncc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].C-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH3;D1;+0:9].[Cl-;H0;D0:10].[NH4+;D0:11].[O;D1;H0:12]=[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:14]2... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and pour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0d22241f43d242af8f693d6d96dc3dca | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1C=CC(NN1)=O.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=S | O=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1.S=P12SP3(=S)SP(=S)(S1)SP(=[S:1])(S2)S3>>[S:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | e0da8be0c0e31372bc487fca4d998b8539b7ff5b84df07e1a6200efd3593e0bb | 13be3f637e1e22872d741944f46b7fcc1954fe982a3a8a0f7825545d455ab147 | S=c1ccc(-c2ccccc2)n[nH]1 | O=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:7])(-S-2)-S-3>>[S;H0;D1;+0:7]=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 187.1 | [{"value": 187.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3×100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thiocarbonyl | c1cccnn1.S1P2SP3SP1SP(S2)S3 | c1cccnn1 | c1cccnn1.c1ccccc1 | Other | N1=CC=CC=C1 | null | null | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>N1=CC=CC=C1>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5442dbabfdcc4f37acb95e22ccc1ca96 | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C(=O)NN)C=C1.ClCC(=O)Cl>>ClCC(=O)NNC(C1=CC=C(C=C1)Cl)=O | [NH2:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl | O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | null | null | O1CCOCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9] | null | [] | null | null | null | null | To a solution of p-chlorobenzoic hydrazide (11.2 g) in dioxane (100 ml) was added chloroacetyl chloride (6 ml). The resulting mixture was refluxed for three hours, cooled to room temperature and filtered. The resulting solid was washed with ethyl ether and dried to yield N'-chloroacetyl-4-chlorobenzoic hydrazide as whi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1 | HCl | O1CCOCC1 | null | null | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>O1CCOCC1>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9eea60a8dcc6414186878ba80c3e84a2 | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>>O=C1NN=C(c2ccc(Cl)cc2)CS1 | BrCC(=O)C1=CC=C(C=C1)Cl.COC(=S)NN>>ClC1=CC=C(C=C1)C1=NNC(SC1)=O | C[O:1][C:2]([NH:3][NH2:4])=[S:14].O=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:13]Br>>[O:1]=[C:2]1[NH:3][N:4]=[C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH2:13][S:14]1 | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1 | O=C1NN=C(c2ccc(Cl)cc2)CS1 | null | null | C(C)#N | Acylation | OtherReaction | a0815ff887854434f061e02bb59e65917f2f792eefe3f407e6f67a241e834044 | b7ddc8c969600ae9a9b2d12841c66a24307741bcbfc0810c56e58eb7d0e4892d | O=C1NN=C(c2ccccc2)CS1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5].C-[O;H0;D2;+0:6]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[#7:9]-[NH2;D1;+0:10]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[#7:9]-[N;H0;D2;+0:10]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[CH2;D2;+0:1]-[S;H0;D2;+0:8]-1 | 48.4 | [{"value": 48.4, "product": "ClC1=CC=C(C=C1)C1=NNC(SC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Ketone.Ether.Thioamide | Hydrazone amide.Monosulfide | null | C1=NNCSC1 | C1=NNCSC1.c1ccccc1 | HBr | C(C)#N | null | null | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>C(C)#N>O=C1NN=C(c2ccc(Cl)cc2)CS1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-27f68e4820374e14ab0032c2fccafbcb | O=C(O)CCC(=O)c1cccc(Cl)c1>>O=C(O)CCCc1cccc(Cl)c1 | ClC=1C=C(C(=O)CCC(=O)O)C=CC1.[OH-].[K+].NN>>ClC=1C=C(C=CC1)CCCC(=O)O | O=[C:6]([CH2:5][CH2:4][C:2](=[O:1])[OH:3])[c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | O=C(O)CCCc1cccc(Cl)c1 | null | null | C(COCCO)O | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[c:7](:[c:8]):[c:9]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:9] | 90.8 | [{"value": 90.8, "product": "ClC=1C=C(C=CC1)CCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 300 ml round-bottomed flask equipped with magnetic stirrer and reflux condenser was charged 23.7 g of 87% potassium hydroxide and 150 ml of diethyleneglycol, With stirring, 23 g of 3-(3-chlorobenzoyl)-propionic acid was added followed by 24 g of 85% hydrazine. The mixture was heated to reflux for 2 hours when 50 m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1 | Other | C(COCCO)O | null | null | O=C(O)CCC(=O)c1cccc(Cl)c1>C(COCCO)O>O=C(O)CCCc1cccc(Cl)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-55b4768f7d654ab4904e96fd665072a4 | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | ClC1=CC=C(C=O)C=C1.C(CCC(=O)C)(=O)O.N1CCCCC1.C1(=CC=CC=C1)C>>ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH3:8].O=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH:8]=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1 | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1 | O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | null | null | O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 44 | [{"value": 44.0, "product": "ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1 | HO- | O | null | null | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>O>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5636ee7c2e944635bdb649b70c7671e3 | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>>COc1ccc(C(=O)O)cc1[N+](=O)[O-] | [N+](=O)([O-])C=1C(=C(C(=O)[O-])C=CC1OC)C.[OH-].[K+]>>[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC | C[c:10]1[c:6]([C:7](=[O:8])[O-:9])[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]1[N+:12](=[O:13])[O-:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-] | COc1ccc(C(=O)O)cc1[N+](=O)[O-] | null | null | O1CCCC1 | Miscellaneous | OtherReaction | ec2bcf645eed3485ae21dd491bac7887e7ecc8e6727067de36c08c87eaa3e98c | d003579d88c8e6390ed4fac608b8ce68d334559ff02e2f3d9c9936750b60a874 | c1ccccc1 | C-[c;H0;D3;+0:1](:[c:2](-[#7;+:3]):[c:4]):[c:5](-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]):[c:9]>>[#7;+:3]-[c:2](:[c:4]):[cH;D2;+0:1]:[c:5](-[C:6](=[O;D1;H0:8])-[OH;D1;+0:7]):[c:9] | 76.6 | [{"value": 76.6, "product": "[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCCC1 | null | 12 | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>O1CCCC1>COc1ccc(C(=O)O)cc1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-748dfcba98824a7cb055ff27a78ee47d | C1CC2=C(C1)O2.CN1CCCC1=Nc1ncnc2nc[nH]c12>>CN1CCCC1=Nc1ncnc2c1ncn2C1C=CC(O)C1 | N1=CN=C2N=CNC2=C1N.O1C2=C1CCC2.P(OC(C)C)(OC(C)C)OC(C)C.CN1C(CCC1)=NC1=C2NC=NC2=NC=N1.CCCCCC.C(CCC)[Li]>>CN1C(CCC1)=NC1=C2N=CN(C2=NC=N1)C1C=CC(C1)O | [CH2:17]1[CH2:18][C:19]2=[C:20]([O:21]2)[CH2:22]1.[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C:6]1=[N:7][c:8]1[n:9][cH:10][n:11][c:12]2[c:13]1[nH:14][cH:15][n:16]2>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C:6]1=[N:7][c:8]1[n:9][cH:10][n:11][c:12]2[c:13]1[n:14][cH:15][n:16]2[CH:17]1[CH:18]=[CH:19][CH:20]([OH:21])[CH2:22]1 | C1CC2=C(C1)O2.CN1CCCC1=Nc1ncnc2nc[nH]c12 | CN1CCCC1=Nc1ncnc2c1ncn2C1C=CC(O)C1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O1CCCC1.CS(=O)C.CC(C)O.CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | bd6c75edf6c43d4b9e90a0af67243778a065f0209402b1ecb4b9780f3e102a87 | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | C1=CC(n2cnc3c(N=C4CCCN4)ncnc32)CC1 | [C:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C;H0;D3;+0:4]2=[C;H0;D3;+0:5]-1-[O;H0;D2;+0:6]-2.[C:7]=[#7:8]-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]2:[n;H0;D2;+0:14]:[c:15]:[nH;D2;+0:16]:[c:17]:2:1>>[C:7]=[#7:8]-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]2:[c:17]:1:[n;H0;D2;+0:16]:[c:15]:[n;H0;D3;+0:14]:2-[CH;D3;+0:2]1-[C:1]-[CH;D3... | 27.1 | [{"value": 27.0, "product": "CN1C(CCC1)=NC1=C2N=CN(C2=NC=N1)C1C=CC(C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.1, "product": "CN1C(CCC1)=NC1=C2N=CN(C2=NC=N1)C1C=CC(C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 224 mg (1 mmol) of palladium(II) acetate, 2.5 ml (10 mmol) of triisopropyl phosphite and 1.5 ml of 1.6 molar n-butyllithium solution in n-hexane (2 mmol) are brought together in 40 ml of dry tetrahydrofuran at 0° C. under inert nitrogen gas and the mixture is stirred. After addition of 30 ml of dry dimethylsulfoxide, 4... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CC2=C(C1)O2.c1ncc2[nH]cnc2n1 | c1ncnc2nc[nH]c12.C1=CCCC1 | C1CC[NH]C1.c1ncnc2nc[nH]c12.C1=CCCC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1.CS(=O)C.CC(C)O.CN1C(CCC1)=O | null | null | C1CC2=C(C1)O2.CN1CCCC1=Nc1ncnc2nc[nH]c12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1.CS(=O)C.CC(C)O.CN1C(CCC1)=O>CN1CCCC1=Nc1ncnc2c1ncn2C1C=CC(O)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-99796af2dfb442b4987e3d94f8747a1f | O=C(OO)c1cccc(Cl)c1>>O=C(O)c1cccc(Cl)c1 | ClC1=CC(=CC=C1)C(=O)OO>>ClC=1C=C(C(=O)O)C=CC1 | O[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([Cl:9])[cH:10]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([Cl:9])[cH:10]1 | O=C(OO)c1cccc(Cl)c1 | O=C(O)c1cccc(Cl)c1 | null | null | C(Cl)Cl | Reduction | OtherReaction | a3a34f0a79d3ff42abf92863db20ba6c8958620c1c833b03092f42d83ad97bb6 | 531425a5a0d611c60dd4e710b59e4cf8c0bfa2d891e7bd03ed5bc1f943ee1b47 | c1ccccc1 | O-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 45.5 | [{"value": 45.5, "product": "ClC=1C=C(C(=O)O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | is stirred with 0.84 g (4.15 mmol) of 85% strength m-chloroperbenzoic acid in 50 ml of methylene chloride at room temperature for 2 days. The precipitate is filtered off with suction, stirred with 50 ml of diethyl ether and filtered off with suction again. The solid residue is dissolved in 2N HCl and the acid aqueous s... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Carboxylic acid | null | null | c1ccccc1 | Other | C(Cl)Cl | null | null | O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>O=C(O)c1cccc(Cl)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6a735af9520a4fa2abe06db3c83e26ae | C1CC2=C(C1)O2.Clc1ncnc2nc[nH]c12>>OC1C=CC(n2cnc3c(Cl)ncnc32)C1 | CO.ClC1=C2NC=NC2=NC=N1.O1C2=C1CCC2>>ClC1=C2N=CN(C2=NC=N1)C1C=CC(C1)O | [O:1]1[C:2]2=[C:3]1[CH2:4][CH2:5][CH2:16]2.[n:6]1[cH:7][nH:8][c:9]2[c:10]([Cl:11])[n:12][cH:13][n:14][c:15]12>>[OH:1][CH:2]1[CH:3]=[CH:4][CH:5]([n:6]2[cH:7][n:8][c:9]3[c:10]([Cl:11])[n:12][cH:13][n:14][c:15]23)[CH2:16]1 | C1CC2=C(C1)O2.Clc1ncnc2nc[nH]c12 | OC1C=CC(n2cnc3c(Cl)ncnc32)C1 | null | [Pd] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | acc6a5533a239bc2114ac47b936794bbf824023062f93501afedefdb9d2efd61 | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | C1=CC(n2cnc3cncnc32)CC1 | [C:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C;H0;D3;+0:4]2=[C;H0;D3;+0:5]-1-[O;H0;D2;+0:6]-2.[Cl;D1;H0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[n;H0;D2;+0:13]:[c:14]:[nH;D2;+0:15]:[c:16]:1:2>>[Cl;D1;H0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[c:16]:1:[n;H0;D2;+0:15]:[c:14]:[n;H0;D3;+0:13]:2-[CH;D3;+0:2]1-[C:1]-[CH;D3;+... | 25 | [{"value": 25.0, "product": "ClC1=C2N=CN(C2=NC=N1)C1C=CC(C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Trimethylsilylated 6-chloropurine (prepared from 50 g (0.32 mol) of 6-chloropurine) is stirred with 5 mol % of the palladium(0) catalyst described above and an equivalent amount of epoxycyclopentene in tetrahydrofuran at room temperature for 24 hours. The reaction solution is heated with methanol for 1.5 hours, the pre... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CC2=C(C1)O2.c1ncc2nc[nH]c2n1 | C1=CCCC1.c1ncnc2[nH]cnc12 | C1=CCCC1.c1ncnc2[nH]cnc12 | null | [Pd].O1CCCC1 | null | null | C1CC2=C(C1)O2.Clc1ncnc2nc[nH]c12>[Pd].O1CCCC1>OC1C=CC(n2cnc3c(Cl)ncnc32)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2a5c50b1454647ab93b2a5a04b014175 | C1CC2=C(C1)O2.Nc1nc2nc[nH]c2c(=O)[nH]1>>Nc1nc2c(ncn2C2C=CC(O)C2)c(=O)[nH]1 | O1C2=C1CCC2.N1C(N)=NC=2N=CNC2C1=O.C[Si](N[Si](C)(C)C)(C)C.S(=O)(=O)([O-])[O-].[NH4+].[NH4+].[SiH3]NC=1NC(C=2NC=NC2N1)=O>>OC1C=CC(C1)N1C=2N=C(NC(C2N=C1)=O)N | [CH2:9]1[CH2:10][C:11]2=[C:12]([O:13]2)[CH2:14]1.[NH2:1][c:2]1[n:3][c:4]2[c:5]([nH:6][cH:7][n:8]2)[c:15](=[O:16])[nH:17]1>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[CH:9]2[CH:10]=[CH:11][CH:12]([OH:13])[CH2:14]2)[c:15](=[O:16])[nH:17]1 | C1CC2=C(C1)O2.Nc1nc2nc[nH]c2c(=O)[nH]1 | Nc1nc2c(ncn2C2C=CC(O)C2)c(=O)[nH]1 | null | [Pd] | O1CCCC1.CO.C=1(C(=CC=CC1)C)C | Heteroatom Alkylation and Arylation | OtherReaction | 2f17178b584520f3811a5df880952686a5cdc311f5900d1e2ebffd1f5dbdf04b | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | O=c1[nH]cnc2c1ncn2C1C=CCC1 | [C:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C;H0;D3;+0:4]2=[C;H0;D3;+0:5]-1-[O;H0;D2;+0:6]-2.[O;D1;H0:7]=[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[n;H0;D2;+0:13]:[c:14]:[nH;D2;+0:15]:[c:16]:1:2>>[O;D1;H0:7]=[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[c:16]:1:[n;H0;D2;+0:15]:[c:14]:[n;H0;D3;+0:13]:2-[CH;D3;+0:2]1-[C:1]-[CH;D3;+0:... | null | [] | null | null | 3 | DAY | 105.8 g (0.7 mol) of guanine are reacted in 600 ml of dry xylene with 500 ml of hexamethyldisilazane and 4 g of ammonium sulfate for 2 days to give the pertrimethylsilyl compound. The oily silylguanine compound is dissolved in 400 ml of dry tetrahydrofuran and the solution is added dropwise to a solution of the palladi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CC2=C(C1)O2.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1=CCCC1 | c1ncc2[nH]cnc2n1.C1=CCCC1 | null | [Pd].O1CCCC1.CO.C=1(C(=CC=CC1)C)C | null | 72 | C1CC2=C(C1)O2.Nc1nc2nc[nH]c2c(=O)[nH]1>[Pd].O1CCCC1.CO.C=1(C(=CC=CC1)C)C>Nc1nc2c(ncn2C2C=CC(O)C2)c(=O)[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f3f413b7f4d24a74988e6718f99f5eee | C1CC2=C(C1)O2.Nc1cc[nH]c(=O)n1>>Nc1ccn(C2C=CC(O)C2)c(=O)n1 | N1C(=O)N=C(N)C=C1.O1C2=C1CCC2.O1CCCC1>>OC1C=CC(C1)N1C(=O)N=C(N)C=C1 | [CH2:6]1[CH2:7][C:8]2=[C:9]([O:10]2)[CH2:11]1.[NH2:1][c:2]1[cH:3][cH:4][nH:5][c:12](=[O:13])[n:14]1>>[NH2:1][c:2]1[cH:3][cH:4][n:5]([CH:6]2[CH:7]=[CH:8][CH:9]([OH:10])[CH2:11]2)[c:12](=[O:13])[n:14]1 | C1CC2=C(C1)O2.Nc1cc[nH]c(=O)n1 | Nc1ccn(C2C=CC(O)C2)c(=O)n1 | null | [Pd] | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 756df0080d4f34ba75dd3dc1a665cf947015af880134f310ecc52f07454f88ed | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | O=c1ncccn1C1C=CCC1 | [C:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C;H0;D3;+0:4]2=[C;H0;D3;+0:5]-1-[O;H0;D2;+0:6]-2.[O;D1;H0:7]=[c:8]1:[#7;a:9]:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[O;D1;H0:7]=[c:8]1:[#7;a:9]:[c:10]:[c:11]:[c:12]:[n;H0;D3;+0:13]:1-[CH;D3;+0:2]1-[C:1]-[CH;D3;+0:5](-[OH;D1;+0:6])-[CH;D2;+0:4]=[CH;D2;+0:3]-1 | 79.2 | [{"value": 79.2, "product": "OC1C=CC(C1)N1C(=O)N=C(N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "OC1C=CC(C1)N1C(=O)N=C(N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | HOUR | 52.5 g (0.47 mol) of cytosine are reacted with 38.5 g (0.47 mol) of epoxycyclopentene at 0° C., by slow addition, in a mixture of in each case 220 ml of dry tetrahydrofuran and dimethylsulfoxide with 1 mol % of the palladium(0) catalyst prepared in situ as described above under an inert argon atmosphere. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CC2=C(C1)O2.c1ccncn1 | c1cncnc1.C1=CCCC1 | c1cncnc1.C1=CCCC1 | null | [Pd].CS(=O)C | null | 90 | C1CC2=C(C1)O2.Nc1cc[nH]c(=O)n1>[Pd].CS(=O)C>Nc1ccn(C2C=CC(O)C2)c(=O)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fbd4497a3b0f42c9919f041b62dbeb0d | C1CC2=C(C1)O2.Cc1c[nH]c(=O)nc1-n1cncn1>>Cc1cn(C2C=CC(O)C2)c(=O)nc1-n1cncn1 | O1C2=C1CCC2.CC=1C(=NC(NC1)=O)N1N=CN=C1>>OC1C=CC(C1)N1C(N=C(C(=C1)C)N1N=CN=C1)=O | [CH2:5]1[CH2:6][C:7]2=[C:8]([O:9]2)[CH2:10]1.[CH3:1][c:2]1[cH:3][nH:4][c:11](=[O:12])[n:13][c:14]1-[n:15]1[cH:16][n:17][cH:18][n:19]1>>[CH3:1][c:2]1[cH:3][n:4]([CH:5]2[CH:6]=[CH:7][CH:8]([OH:9])[CH2:10]2)[c:11](=[O:12])[n:13][c:14]1-[n:15]1[cH:16][n:17][cH:18][n:19]1 | C1CC2=C(C1)O2.Cc1c[nH]c(=O)nc1-n1cncn1 | Cc1cn(C2C=CC(O)C2)c(=O)nc1-n1cncn1 | null | [Pd] | O1CCCC1.CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | cd185d9f701f2f58c7a794d39035dcbcfaa3848606185560bd6789895616bcf5 | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | O=c1nc(-n2cncn2)ccn1C1C=CCC1 | [C:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C;H0;D3;+0:4]2=[C;H0;D3;+0:5]-1-[O;H0;D2;+0:6]-2.[O;D1;H0:7]=[c:8]1:[#7;a:9]:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[O;D1;H0:7]=[c:8]1:[#7;a:9]:[c:10]:[c:11]:[c:12]:[n;H0;D3;+0:13]:1-[CH;D3;+0:2]1-[C:1]-[CH;D3;+0:5](-[OH;D1;+0:6])-[CH;D2;+0:4]=[CH;D2;+0:3]-1 | 25.8 | [{"value": 25.8, "product": "OC1C=CC(C1)N1C(N=C(C(=C1)C)N1N=CN=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | The equivalent amount of epoxycyclopentene is slowly added at 0° C. to 3.54 g (0.020 mol) of 5-methyl-4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (prepared by reaction of thymine with 1,2,4-triazole/POCl3 /triethylamine) in a mixture of 40 ml of dry tetrahydrofuran and 20 ml of dry dimethylsulfoxide with 5 mol % of the p... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CC2=C(C1)O2.c1cncnc1 | c1cncnc1.C1=CCCC1 | c1cncnc1.C1=CCCC1.c1nc[nH]n1 | null | [Pd].O1CCCC1.CS(=O)C | null | 12 | C1CC2=C(C1)O2.Cc1c[nH]c(=O)nc1-n1cncn1>[Pd].O1CCCC1.CS(=O)C>Cc1cn(C2C=CC(O)C2)c(=O)nc1-n1cncn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3631cb4a220a4c79b2f3de3655e204e2 | C1CC2=C(C1)O2.Cc1c[nH]c(=O)nc1N>>Cc1cn(C2C=CC(O)C2)c(=O)nc1N | CS(=O)C.CC=1C(=NC(NC1)=O)N.O1C2=C1CCC2>>NC1=NC(N(C=C1C)C1C=CC(C1)O)=O | [CH2:5]1[CH2:6][C:7]2=[C:8]([O:9]2)[CH2:10]1.[CH3:1][c:2]1[cH:3][nH:4][c:11](=[O:12])[n:13][c:14]1[NH2:15]>>[CH3:1][c:2]1[cH:3][n:4]([CH:5]2[CH:6]=[CH:7][CH:8]([OH:9])[CH2:10]2)[c:11](=[O:12])[n:13][c:14]1[NH2:15] | C1CC2=C(C1)O2.Cc1c[nH]c(=O)nc1N | Cc1cn(C2C=CC(O)C2)c(=O)nc1N | null | [Pd] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | cd185d9f701f2f58c7a794d39035dcbcfaa3848606185560bd6789895616bcf5 | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | O=c1ncccn1C1C=CCC1 | [C:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C;H0;D3;+0:4]2=[C;H0;D3;+0:5]-1-[O;H0;D2;+0:6]-2.[O;D1;H0:7]=[c:8]1:[#7;a:9]:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[O;D1;H0:7]=[c:8]1:[#7;a:9]:[c:10]:[c:11]:[c:12]:[n;H0;D3;+0:13]:1-[CH;D3;+0:2]1-[C:1]-[CH;D3;+0:5](-[OH;D1;+0:6])-[CH;D2;+0:4]=[CH;D2;+0:3]-1 | 24.4 | [{"value": 24.4, "product": "NC1=NC(N(C=C1C)C1C=CC(C1)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.4, "product": "NC1=NC(N(C=C1C)C1C=CC(C1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 50 g (0.4 mol) of 5-methylcytosine are added to a solution of the palladium(0) catalyst (1.6 mol %) prepared in situ as described above in 200 ml of dry tetrahydrofuran/200 ml of dry dimethylsulfoxide at 5° C. 49.2 g (0.6 mol) of epoxycyclopentene, dissolved in 100 ml of tetrahydrofuran, are added dropwise to this susp... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CC2=C(C1)O2.c1cncnc1 | c1cncnc1.C1=CCCC1 | c1cncnc1.C1=CCCC1 | null | [Pd].O1CCCC1 | null | 1.5 | C1CC2=C(C1)O2.Cc1c[nH]c(=O)nc1N>[Pd].O1CCCC1>Cc1cn(C2C=CC(O)C2)c(=O)nc1N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8948fd82469d40509bd6a261a8fe67b3 | C1CC2=C(C1)O2.O=c1cccc[nH]1>>O=c1ccccn1C1C=CC(O)C1 | N1C(C=CC=C1)=O.O1C2=C1CCC2>>OC1C=CC(C1)N1C(C=CC=C1)=O | [CH2:8]1[CH2:9][C:10]2=[C:11]([O:12]2)[CH2:13]1.[O:1]=[c:2]1[cH:3][cH:4][cH:5][cH:6][nH:7]1>>[O:1]=[c:2]1[cH:3][cH:4][cH:5][cH:6][n:7]1[CH:8]1[CH:9]=[CH:10][CH:11]([OH:12])[CH2:13]1 | C1CC2=C(C1)O2.O=c1cccc[nH]1 | O=c1ccccn1C1C=CC(O)C1 | null | [Pd].C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 46c8cce012641dbcb1634e3d4e598de2ff15e9a3420dd6268f6a2dd60fe5bf82 | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | O=c1ccccn1C1C=CCC1 | [C:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C;H0;D3;+0:4]2=[C;H0;D3;+0:5]-1-[O;H0;D2;+0:6]-2.[O;D1;H0:7]=[c:8](:[c:9]):[nH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H0:7]=[c:8](:[c:9]):[n;H0;D3;+0:10](-[CH;D3;+0:2]1-[C:1]-[CH;D3;+0:5](-[OH;D1;+0:6])-[CH;D2;+0:4]=[CH;D2;+0:3]-1):[c:11]:[c:12] | 18.5 | [{"value": 18.49, "product": "OC1C=CC(C1)N1C(C=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.5, "product": "OC1C=CC(C1)N1C(C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 21 g (0.22 mol) of 2-pyridone are added at 0° C. to a solution of the palladium(0) catalyst prepared as above (2 mol % of palladium(II) acetate) in 200 ml of dry tetrahydrofuran, and 20.1 g (0.245 mol) of epoxycyclopentene, dissolved in 80 ml of tetrahydrofuran, are then added dropwise over a period of 2 hours, while s... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CC2=C(C1)O2.c1ccccn1 | c1ccncc1.C1=CCCC1 | c1ccncc1.C1=CCCC1 | null | [Pd].C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1 | null | null | C1CC2=C(C1)O2.O=c1cccc[nH]1>[Pd].C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1>O=c1ccccn1C1C=CC(O)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6e14b0ec78f34ee0b298c7c757c73c4b | C1=CC2OC2CC1.Nc1ncnc2nc[nH]c12>>Nc1ncnc2c1ncn2C1C=CC(O)CC1 | P(OC(C)C)(OC(C)C)OC(C)C.O1C2C=CCCC21.C(CCC)[Li].N1=CN=C2N=CNC2=C1N>>OC1C=CC(CC1)N1C2=NC=NC(=C2N=C1)N | [CH:11]12[CH:12]=[CH:13][CH2:17][CH2:16][CH:14]1[O:15]2.[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[nH:8][cH:9][n:10]2>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[CH:11]1[CH:12]=[CH:13][CH:14]([OH:15])[CH2:16][CH2:17]1 | C1=CC2OC2CC1.Nc1ncnc2nc[nH]c12 | Nc1ncnc2c1ncn2C1C=CC(O)CC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].[Pd] | O1CCCC1.CCCCCC.CS(=O)C.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 165e4573208c5687dbf93d74cc652eda120616a6a5228ae81852e0d2a05c9c0c | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | C1=CC(n2cnc3cncnc32)CCC1 | [C:1]1=[CH;D2;+0:2]-[CH2;D2;+0:3]-[C:4]-[CH;D3;+0:5]2-[O;H0;D2;+0:6]-[CH;D3;+0:7]-1-2.[N;D1;H2:8]-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]2:[n;H0;D2;+0:14]:[c:15]:[nH;D2;+0:16]:[c:17]:1:2>>[N;D1;H2:8]-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]2:[c:17]:1:[n;H0;D2;+0:16]:[c:15]:[n;H0;D3;+0:14]:2-[CH;D3;+0:7]1-[C:1]=[CH;D2;... | 36.9 | [{"value": 36.9, "product": "OC1C=CC(CC1)N1C2=NC=NC(=C2N=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.9, "product": "OC1C=CC(CC1)N1C2=NC=NC(=C2N=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | The palladium(0) catalyst is prepared by bringing together 179.6 mg of palladium(II) acetate, 2 ml of triisopropyl phosphite and 1.06 ml of a 1.4 molar solution of butyllithium in n-hexane in 60 ml of dry tetrahydrofuran at 0° C. under argon. 60 ml of dry dimethylsulfoxide and 17.32 g (0.128 mol) of adenine are then ad... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1=CC2OC2CC1.c1ncc2[nH]cnc2n1 | c1ncnc2nc[nH]c12.C1=CCCCC1 | c1ncnc2nc[nH]c12.C1=CCCCC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].[Pd].O1CCCC1.CCCCCC.CS(=O)C.C(C)O | null | 0.25 | C1=CC2OC2CC1.Nc1ncnc2nc[nH]c12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].[Pd].O1CCCC1.CCCCCC.CS(=O)C.C(C)O>Nc1ncnc2c1ncn2C1C=CC(O)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f41944dbd74a452ebef29c79fa256e46 | C1=CC2OC2CC1.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1C1C=CCCC1O | C1(C=2C(C(N1)=O)=CC=CC2)=O.O1C2C=CCCC21>>OC1C(C=CCC1)N1C(C=2C(C1=O)=CC=CC2)=O | [CH:12]12[CH:13]=[CH:14][CH2:15][CH2:16][CH:17]1[O:18]2.[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH:12]1[CH:13]=[CH:14][CH2:15][CH2:16][CH:17]1[OH:18] | C1=CC2OC2CC1.O=C1NC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1C1C=CCCC1O | null | [Pd] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 4bed6287f54cdebfc771940611efec6af95f20ad6784f7b71026182628045af3 | f10eca2bf3fa1dcad323f831f8ff7310de25690c46b42e2221565f28d8de59bb | O=C1c2ccccc2C(=O)N1C1C=CCCC1 | [C:1]1=[C:2]-[C:3]-[C:4]-[C:5]2-[O;H0;D2;+0:6]-[CH;D3;+0:7]-1-2.[O;D1;H0:8]=[C:9]1-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[c:13]:[c:14]-1>>[O;D1;H0:8]=[C:9]1-[c:14]:[c:13]-[C:11](=[O;D1;H0:12])-[N;H0;D3;+0:10]-1-[CH;D3;+0:7]1-[C:1]=[C:2]-[C:3]-[C:4]-[C:5]-1-[OH;D1;+0:6] | null | [] | null | null | null | null | If 19.11 g (0.13 mol) of phthalimide are reacted with 0.6 mol % of the palladium(0) catalyst prepared in situ as described above and one equivalent of 3,4-epoxycyclohexene in tetrahydrofuran first at 0° C. and then for 4 hours at the reflux temperature, 1.45 g (4.6% of theory) of [(1RS,2SR)-2-hydroxy-1-phthalimido-cycl... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Unsubstituted dicarboximide | Substituted dicarboximide.Secondary alcohol | C1=CC2OC2CC1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2.C1=CCCCC1 | c1ccc2c(c1)C[NH]C2.C1=CCCCC1 | null | [Pd].O1CCCC1 | null | null | C1=CC2OC2CC1.O=C1NC(=O)c2ccccc21>[Pd].O1CCCC1>O=C1c2ccccc2C(=O)N1C1C=CCCC1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d5b2880797f74a08a7cbbba9fab2e5b9 | C1=CC2OC2CC1.Nc1nc2nc[nH]c2c(=O)[nH]1>>Nc1nc2c(ncn2C2C=CC(O)CC2)c(=O)[nH]1 | N1C(N)=NC=2N=CNC2C1=O.O1C2C=CCCC21.CO>>OC1C=CC(CC1)N1C=2N=C(NC(C2N=C1)=O)N | [CH:9]12[CH:12]([CH:11]=[CH:10][CH2:14][CH2:15]1)[O:13]2.[NH2:1][c:2]1[n:3][c:4]2[c:5]([nH:6][cH:7][n:8]2)[c:16](=[O:17])[nH:18]1>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[CH:9]2[CH:10]=[CH:11][CH:12]([OH:13])[CH2:14][CH2:15]2)[c:16](=[O:17])[nH:18]1 | C1=CC2OC2CC1.Nc1nc2nc[nH]c2c(=O)[nH]1 | Nc1nc2c(ncn2C2C=CC(O)CC2)c(=O)[nH]1 | null | [Pd] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 386f10f90329eb8b74e7564d1c3fd964fab46e634b6fb61d92155b5d8d96b0af | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | O=c1[nH]cnc2c1ncn2C1C=CCCC1 | [C:1]1=[CH;D2;+0:2]-[CH2;D2;+0:3]-[C:4]-[CH;D3;+0:5]2-[O;H0;D2;+0:6]-[CH;D3;+0:7]-1-2.[O;D1;H0:8]=[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]2:[n;H0;D2;+0:14]:[c:15]:[nH;D2;+0:16]:[c:17]:1:2>>[O;D1;H0:8]=[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]2:[c:17]:1:[n;H0;D2;+0:16]:[c:15]:[n;H0;D3;+0:14]:2-[CH;D3;+0:5]1-[C:4]-[CH2;D2... | 25.1 | [{"value": 25.1, "product": "OC1C=CC(CC1)N1C=2N=C(NC(C2N=C1)=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7.56 g (50 mmol) of guanine are reacted with 2 mol % of the palladium(0) catalyst prepared in situ as above and one equivalent of 3,4-epoxycyclohexene in tetrahydrofuran first at 0° C. and then for 8 hours under reflux temperature, and the mixture is then poured into methanol. The reaction mixture is concentrated and t... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1=CC2OC2CC1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1=CCCCC1 | c1ncc2[nH]cnc2n1.C1=CCCCC1 | null | [Pd].O1CCCC1 | null | null | C1=CC2OC2CC1.Nc1nc2nc[nH]c2c(=O)[nH]1>[Pd].O1CCCC1>Nc1nc2c(ncn2C2C=CC(O)CC2)c(=O)[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-21c19f7a233c45f48e57d49008b757a2 | C1=CC2OC2CC1.Cc1c[nH]c(=O)[nH]c1=O>>Cc1cn(C2=CCC(O)CC2)c(=O)[nH]c1=O | N1C(=O)NC(=O)C(C)=C1.O1C2C=CCCC21.CO>>OC1CC=C(CC1)N1C(=O)NC(=O)C(C)=C1 | [CH:5]12[CH:8]([CH:7]=[CH:6][CH2:10][CH2:11]1)[O:9]2.[CH3:1][c:2]1[cH:3][nH:4][c:12](=[O:13])[nH:14][c:15]1=[O:16]>>[CH3:1][c:2]1[cH:3][n:4]([C:5]2=[CH:6][CH2:7][CH:8]([OH:9])[CH2:10][CH2:11]2)[c:12](=[O:13])[nH:14][c:15]1=[O:16] | C1=CC2OC2CC1.Cc1c[nH]c(=O)[nH]c1=O | Cc1cn(C2=CCC(O)CC2)c(=O)[nH]c1=O | null | [Pd] | O1CCCC1 | Functional Group Interconversion | OtherReaction | 6a62294476deb82b4c63d7876752f097f3dabbf3ba098bcf4543ce66670e7c37 | b8d70aaa95913b8be6c6458586b32660eefbc92f5b2328684f0a9032d1e0c679 | O=c1ccn(C2=CCCCC2)c(=O)[nH]1 | [C:1]1-[CH2;D2;+0:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[CH;D3;+0:5]2-[O;H0;D2;+0:6]-[CH;D3;+0:7]-1-2.[O;D1;H0:8]=[c:9]1:[#7;a:10]:[c:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[O;D1;H0:8]=[c:9]1:[#7;a:10]:[c:11]:[c:12]:[c:13]:[n;H0;D3;+0:14]:1-[C;H0;D3;+0:7]1=[CH;D2;+0:3]-[CH2;D2;+0:4]-[CH;D3;+0:5](-[OH;D1;+0:6])-[CH2;D2;+0:2]-[C:1]-1 | 16.2 | [{"value": 16.2, "product": "OC1CC=C(CC1)N1C(=O)NC(=O)C(C)=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 6.3 g (50 mmol) of thymine are treated with 2 mol % of the palladium(0) catalyst prepared in situ as described above and with one equivalent of 3,4-epoxycyclohexene in tetrahydrofuran first at 0° C. and then for 4 hours at the reflux temperature. Methanol is added to the reaction mixture, the suspension is filtered, th... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1=CC2OC2CC1.c1cncnc1 | c1cncnc1.C1=CCCCC1 | c1cncnc1.C1=CCCCC1 | null | [Pd].O1CCCC1 | null | 4 | C1=CC2OC2CC1.Cc1c[nH]c(=O)[nH]c1=O>[Pd].O1CCCC1>Cc1cn(C2=CCC(O)CC2)c(=O)[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-330f55c398084380a21ed3bc9f782a5c | N#Cc1cc(F)c(Cl)c(Cl)c1Cl.[F-]>>N#Cc1cc(F)c(F)c(Cl)c1F | ClC1=C(C#N)C=C(C(=C1Cl)Cl)F.N(=O)[O-].[Na+].F[B-](F)(F)F.[Na+].ClC1=C(C#N)C=C(C(=C1Cl)Cl)F.[F-].[K+]>>ClC=1C(=C(C#N)C=C(C1F)F)F | Cl[c:7]1[c:5]([F:6])[cH:4][c:3]([C:2]#[N:1])[c:11](Cl)[c:9]1[Cl:10].[F-:12]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[c:7]([F:8])[c:9]([Cl:10])[c:11]1[F:12] | N#Cc1cc(F)c(Cl)c(Cl)c1Cl.[F-] | N#Cc1cc(F)c(F)c(Cl)c1F | null | null | CS(=O)C | Functional Group Interconversion | OtherReaction | f99eb4cee730f330d9063e887b7b098c500f8094a635b09908b9426360b274dc | a95243d67cc16a7ad5c833bb40412cb54c45ecf5caf39d7aa98e12eb2dcb28fe | c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[c:6](-[F;D1;H0:7]):[c;H0;D3;+0:8](-Cl):[c:9]:1-[Cl;D1;H0:10].[F-;H0;D0:11]>>[Cl;D1;H0:10]-[c:9]1:[c;H0;D3;+0:1](-[F;H0;D1;+0:11]):[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[c:6](-[F;D1;H0:7]):[c;H0;D3;+0:8]:1-[F;D1;H0:12] | null | [] | null | null | null | null | The reduction of 2,3,4-trichloro-5-fluoronitrobenzene (i) with Fe-HCI in hot water gives 2,3,4-trichloro-5-fluoroaniline (ii), which, by diazotization with NaNO2 -HCI and reaction with sodium tetra-fluoroborate and cuprous cyanide, is converted to 2,3,4-trichloro-5-fluorobenzonitrile (iii). The reaction of (iii) with K... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | Aromatic halide.Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CS(=O)C | null | null | N#Cc1cc(F)c(Cl)c(Cl)c1Cl.[F-]>CS(=O)C>N#Cc1cc(F)c(F)c(Cl)c1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5744dc58454a4ec19d043fe07502ce29 | CCOC(=O)CC(=O)c1cc(F)c(F)c(Cl)c1F.CCOC(OCC)OCC>>CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)c(Cl)c1F | ClC=1C(=C(C(=O)CC(=O)OCC)C=C(C1F)F)F.C(OCC)(OCC)OCC.C(C)(=O)OC(C)=O>>ClC=1C(=C(C(=O)C(C(=O)OCC)=COCC)C=C(C1F)F)F | [CH2:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[cH:14][c:15]([F:16])[c:17]([F:18])[c:19]([Cl:20])[c:21]1[F:22].CCO[CH:4](OCC)[O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH:4]=[C:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[cH:14][c:15]([F:16])[c:17]([F:18])[c:19]([Cl:20])[c:21]1[F:22] | CCOC(=O)CC(=O)c1cc(F)c(F)c(Cl)c1F.CCOC(OCC)OCC | CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)c(Cl)c1F | null | null | null | C-C Coupling | OtherReaction | 7cfff3053680512afd8f3daf149645dfb2cfa4c9c32bf9b885b72097190aacf2 | 9164ecc9bc41a60ea056ee2b5a56d6c3899e2ff7c236ad9974338a128257f79c | c1ccccc1 | C-C-O-[CH;D3;+0:1](-O-C-C)-[#8:2]-[C:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C:3]-[#8:2]-[CH;D2;+0:1]=[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[c:11])-[C:6](=[O;D1;H0:7])-[#8:5]-[C:4] | null | [] | null | null | null | null | The reduction of 2,3,4-trichloro-5-fluoronitrobenzene (i) with Fe-HCI in hot water gives 2,3,4-trichloro-5-fluoroaniline (ii), which, by diazotization with NaNO2 -HCI and reaction with sodium tetra-fluoroborate and cuprous cyanide, is converted to 2,3,4-trichloro-5-fluorobenzonitrile (iii). The reaction of (iii) with K... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether.Ether.Ether | Ketone.Ester.Ether | null | null | c1ccccc1 | HO- | null | null | null | CCOC(=O)CC(=O)c1cc(F)c(F)c(Cl)c1F.CCOC(OCC)OCC>>CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)c(Cl)c1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9f7703e48cbb46a1bf4734a16320244e | C1CN=C2CCCN2C1.O=C(O)[C@@H]1CCCN1>>C1=C2CNCC2NCC1 | N1[C@H](C(=O)O)CCC1.N12CCCCCC2=NCCC1.N=C=N.N12CCCN=C2CCC1>>C12NCCC=C2CNC1 | C1C[CH2:3][N:4]2[C:2](=N1)[CH2:6]C[CH2:5]2.O=C(O)[C@@H]1[CH2:1][CH2:9][CH2:8][NH:7]1>>[CH:1]1=[C:2]2[CH2:3][NH:4][CH2:5][CH:6]2[NH:7][CH2:8][CH2:9]1 | C1CN=C2CCCN2C1.O=C(O)[C@@H]1CCCN1 | C1=C2CNCC2NCC1 | null | null | C(C)#N.C(C)N(CC)CC.C(Cl)(Cl)Cl.CS(=O)C.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | f0e5412bf8d665286e5ba4b14b361509e035dde21ea4ad80cf97903bbea8948d | ee13ed889cc66f9c8cb0daf14dadf6acf2d7341c19647ce34a3cfeff122ee714 | C1=C2CNCC2NCC1 | C1-C-[CH2;D2;+0:1]-[N;H0;D3;+0:2]2-[CH2;D2;+0:3]-C-[CH2;D2;+0:4]-[C;H0;D3;+0:5]-2=N-1.O-C(=O)-[C@H]1-[CH2;D2;+0:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[C:8]1-[C:7]-[CH;D2;+0:6]=[C;H0;D3;+0:5]2-[CH2;D2;+0:1]-[NH;D2;+0:2]-[CH2;D2;+0:3]-[CH;D3;+0:4]-2-[NH;D2;+0:9]-1 | null | [] | null | null | null | null | Compound (II) is reacted with N-tosyl-L-prolyl chloride in an organic solvent such as methylene chloride or chloroform or in a mixture of water and the said organic solvents in the presence of an organic base such as triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine.Tertiary amine | Secondary amine.Secondary amine | C1CN=C2CCCN2C1.C1CCNC1 | C1=C2CNCC2NCC1 | C1=C2CNCC2NCC1 | HO- | C(C)#N.C(C)N(CC)CC.C(Cl)(Cl)Cl.CS(=O)C.CN(C=O)C | null | null | C1CN=C2CCCN2C1.O=C(O)[C@@H]1CCCN1>C(C)#N.C(C)N(CC)CC.C(Cl)(Cl)Cl.CS(=O)C.CN(C=O)C>C1=C2CNCC2NCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2d957fe77de8410f95f25968890c9172 | CCOC(=O)C1CN(Cc2ccccc2)CC1=O.NCc1ccccc1>>CCOC(=O)C1CN(Cc2ccccc2)CC1NCc1ccccc1 | C(C1=CC=CC=C1)N1CC(C(C1)=O)C(=O)OCC.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)N1CC(C(C1)NCC1=CC=CC=C1)C(=O)OCC | O=[C:17]1[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1.[NH2:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH:17]1[NH:18][CH2:19][c... | CCOC(=O)C1CN(Cc2ccccc2)CC1=O.NCc1ccccc1 | CCOC(=O)C1CN(Cc2ccccc2)CC1NCc1ccccc1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Reductive amination with ketone | effc44ed4b067dc0411f40af490f2a58460658ca21c3907f6738fc01545dfd2a | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CNC2CCN(Cc3ccccc3)C2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-[C:6]-1-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[NH2;D1;+0:11]-[C:12]-[c:13]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C:6]1-[C:5]-[#7:3](-[C:4])-[C:2]-[CH;D3;+0:1]-1-[NH;D2;+0:11]-[C:12]-[c:13] | 71 | [{"value": 71.0, "product": "C(C1=CC=CC=C1)N1CC(C(C1)NCC1=CC=CC=C1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "C(C1=CC=CC=C1)N1CC(C(C1)NCC1=CC=CC=C1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 24.7 g of 1-benzyl-3-carboethoxy-4-pyrrolidone and 10.7 g of benzylamine were added to 100 ml of benzene, and then dehydrated with Dean-Stark distillation apparatus. The residual benzene was evaporated. The residue was dissolved in 200 ml of tetrahydrofuran, and then a small amount of methyl orange was added. To this w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccccc1 | Other | C1=CC=CC=C1 | null | null | CCOC(=O)C1CN(Cc2ccccc2)CC1=O.NCc1ccccc1>C1=CC=CC=C1>CCOC(=O)C1CN(Cc2ccccc2)CC1NCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ac645281b4e549e4b05f16b0f998358d | CC(C)(C)OC(=O)N1CC2=CCCN(C(=O)OC(C)(C)C)C2C1>>C1=C2CNCC2NCC1.Cl | Cl.C(C)(C)(C)OC(=O)N1CC2=CCCN(C2C1)C(=O)OC(C)(C)C>>Cl.Cl.C12NCCC=C2CNC1 | CC(C)(C)OC(=O)[N:4]1[CH2:3][C:2]2=[CH:1][CH2:9][CH2:8][N:7](C(=O)OC(C)(C)C)[CH:6]2[CH2:5]1>>[CH:1]1=[C:2]2[CH2:3][NH:4][CH2:5][CH:6]2[NH:7][CH2:8][CH2:9]1.[ClH:11] | CC(C)(C)OC(=O)N1CC2=CCCN(C(=O)OC(C)(C)C)C2C1 | C1=C2CNCC2NCC1.Cl | null | null | CO | Miscellaneous | OtherReaction | 2a44f0a18ed374630ed1d611cbbbe6f3763340e1b2bb6f4eef1be3ebebe4ca4c | 3c4f51b1c1f508215f616109a3309695a74a7c119e69c8c1a7e8536489a089af | C1=C2CNCC2NCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]2=[C:4]-[C:5]-[C:6]-[N;H0;D3;+0:7](-C(=O)-O-C(-C)(-C)-C)-[C:8]-2-[C:9]-1>>[C:4]1=[C:3]2-[C:2]-[NH;D2;+0:1]-[C:9]-[C:8]-2-[NH;D2;+0:7]-[C:6]-[C:5]-1 | null | [] | null | null | 4 | HOUR | To 30 ml of methanol saturated with hydrogen chloride gas was added 9.72 g of N,N'-di-t-butoxycarbonyl-2,8-diazabicyclo[4.3.0]non-5-ene, stirred at room temperature for 4 hours, and then evaporated under reduced pressure to obtain 5.85 g of the desired compound.
Conditions: See reaction.notes.procedure_details.
Workup:... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine.Secondary amine | C1=C2C[NH]CC2[NH]CC1 | C1=C2CNCC2NCC1 | C1=C2CNCC2NCC1 | HO- | CO | null | 4 | CC(C)(C)OC(=O)N1CC2=CCCN(C(=O)OC(C)(C)C)C2C1>CO>C1=C2CNCC2NCC1.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6acf705f7b21407b95eaae261c75e22c | Clc1ccncc1.Cn1ccc2cc(N)ccc21>>Cn1ccc2cc(Nc3ccncc3)ccc21 | O.Cl.ClC1=CC=NC=C1.NC=1C=C2C=CN(C2=CC1)C.C([O-])([O-])=O.[Na+].[Na+].Cl.ClC1=CC=NC=C1>>CN1C=CC2=CC(=CC=C12)NC1=CC=NC=C1 | Cl[c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1.[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH2:8])[cH:15][cH:16][c:17]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH:8][c:9]3[cH:10][cH:11][n:12][cH:13][cH:14]3)[cH:15][cH:16][c:17]12 | Clc1ccncc1.Cn1ccc2cc(N)ccc21 | Cn1ccc2cc(Nc3ccncc3)ccc21 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3[nH]ccc3c2)ccn1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:10] | 53.3 | [{"value": 53.3, "product": "CN1C=CC2=CC(=CC=C12)NC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloropyridine hydrochloride (8 g) was added to a solution of 5-amino-1-methylindole (7 g) in 75 ml 1-methyl-2-pyrrolidinone preheated to 100° C. The addition of 4-chloropyridine hydrochloride (4 g) after one hour caused no further reaction as determined by TLC. After two hours the reaction mixture was cooled, stirre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2[nH]ccc2c1.c1ccncc1 | HCl | CN1C(CCC1)=O | null | null | Clc1ccncc1.Cn1ccc2cc(N)ccc21>CN1C(CCC1)=O>Cn1ccc2cc(Nc3ccncc3)ccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3a6f2a39155f44088f6340ad34bee87b | COC(=O)Cl.Cn1ccc2cc(Nc3ccncc3)ccc21>>COC(=O)N(c1ccncc1)c1ccc2c(ccn2C)c1 | ClC(=O)OC.CN1C=CC2=CC(=CC=C12)NC1=CC=NC=C1>>COC(N(C1=CC=NC=C1)C=1C=C2C=CN(C2=CC1)C)=O | Cl[C:3]([O:2][CH3:1])=[O:4].[NH:5]([c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17][cH:18][n:19]2[CH3:20])[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17][cH:18][n:19]2[CH3:20])[cH:21]1 | COC(=O)Cl.Cn1ccc2cc(Nc3ccncc3)ccc21 | COC(=O)N(c1ccncc1)c1ccc2c(ccn2C)c1 | null | null | C(C)N(CC)CC.C(Cl)Cl | Protection | N-alkylation of secondary amines with alkyl halides | 496a200c7c2fc7c000296e03cda40efb8e258ccaeb02fa999285bf74ddc49346 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | c1cc(Nc2ccc3[nH]ccc3c2)ccn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[c:5]:[c:6](-[NH;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1):[c:14]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[c:6](:[c:5]):[c:14])-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1 | 98.4 | [{"value": 98.4, "product": "COC(N(C1=CC=NC=C1)C=1C=C2C=CN(C2=CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of methyl chloroformate (1.3 g) in 5 ml DCM was added to a solution of 1-methyl-5-(4-pyridinylamino)-1H-indole (2.5 g) in 120 ml DCM and 6 ml triethylamine (4.4 g). After stirring one hour at ambient temperature the reaction mixture was washed with water and saturated sodium chloride, dried (anhydrous magnes... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | null | null | c1ccncc1.c1ccc2[nH]ccc2c1 | HCl | C(C)N(CC)CC.C(Cl)Cl | null | 1 | COC(=O)Cl.Cn1ccc2cc(Nc3ccncc3)ccc21>C(C)N(CC)CC.C(Cl)Cl>COC(=O)N(c1ccncc1)c1ccc2c(ccn2C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-530fd71ea9dc478c961cb83e7425e289 | CCCCC#CCCO>>C#CCCCCCCO | NCCCN.C(CC#CCCCC)O>>C(CCCCCC#C)O | [C:1]([CH2:2][CH2:3][CH2:4][CH3:5])#[C:6][CH2:7][CH2:8][OH:9]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9] | CCCCC#CCCO | C#CCCCCCCO | null | null | CCCCCC | Functional Group Interconversion | OtherReaction | 717941f395a910361dbd079f0406c8739db3d600df9659ab84f995c3dd1e77a5 | f5163dfbf670ee9f38d1be788eef0e0a983df5868f48fe01d48741d6a3f98157 | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[CH2;D2;+0:5]-[C:6]-[C:7]-[CH3;D1;+0:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:8]-[C:7]-[C:6]-[C;H0;D2;+0:5]#[CH;D1;+0:4] | null | [] | null | null | null | null | 35% KH in mineral oil (27 g, 240 mmol) under an argon atmosphere was washed with hexane and treated dropwise with 1,3-diaminopropane. The mixture was stirred at room temperature until it became homogeneous. The flask was cooled to 0∞C and 3-octyn-1-ol (10 g, 79 mmol, Lancaster Synthesis) was slowly added. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | null | null | null | null | CCCCCC | null | null | CCCCC#CCCO>CCCCCC>C#CCCCCCCO |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-67b9731ed76841a881947f558c2f930d | CCCCC#CCCO>>C#CCCCCCCO | C(CC#CCCCC)O.[H-].[K+].NCCCN>>C(CCCCCC#C)O | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][OH:9]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9] | CCCCC#CCCO | C#CCCCCCCO | null | null | CCCCCC | Miscellaneous | OtherReaction | 1dc82b94ad0bb9c37129929afef1fa70f760dcdf2017a728c72d09b3d0dbf429 | 7b33466a2cc81bfe95f125510ec1a59cf92dd3caaf14f1a960631fc63bb0a68b | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5]-[C:6]-[CH2;D2;+0:7]-[CH3;D1;+0:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5]-[C:6]-[C;H0;D2;+0:7]#[CH;D1;+0:8] | null | [] | null | null | null | null | Potassium hydride, (35%) in mineral oil (27 g, 240 mmol) under an argon atmosphere was washed with hexane and treated dropwise with 1,3-diaminopropane. The mixture was stirred at room temperature until it became homogeneous. The flask was cooled to 0° C. and 3-octyn-1-ol (10 g, 79 mmol, Lancaster Synthesis) was slowly ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | null | null | null | null | CCCCCC | null | null | CCCCC#CCCO>CCCCCC>C#CCCCCCCO |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c4ad1e1a6d38490b99bef88812616636 | CCCCCCCCCCCCOc1ccc(C)nc1/C=C/CC(=O)O.O=C(OO)c1cccc(Cl)c1>>CCCCCCCCCCCCOc1ccc(C)[n+]([O-])c1C=CCC(=O)O | C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCCCCC)C.ClC=1C=C(C(=O)OO)C=CC1.C(=O)(O)[O-].[Na+]>>C(=O)(O)CC=CC1=[N+](C(=CC=C1OCCCCCCCCCCCC)C)[O-] | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17]([CH3:18])[n:19][c:21]1/[CH:22]=[CH:23]/[CH2:24][C:25](=[O:26])[OH:27].O=C(O[OH:20])c1cccc(Cl)c1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[c... | CCCCCCCCCCCCOc1ccc(C)nc1/C=C/CC(=O)O.O=C(OO)c1cccc(Cl)c1 | CCCCCCCCCCCCOc1ccc(C)[n+]([O-])c1C=CCC(=O)O | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1cc[nH+]cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6](-[C:7]=[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13] | null | [] | null | null | 16 | HOUR | 2-(E-2-Carboxymethylethenyl)-3-dodecyloxy-6-methylpyridine (2.15 g, 5.95 mmol) was dissolved in dry CH2Cl2 (20 mL) and cooled to 0∞C; 85% m-chloroperoxybenzoic acid (1.45 g, 7.14 mmol) was added and the reaction was stirred at 0∞C for 30 minutes and at room temperature for 16 hours. The reaction solution was poured int... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HCl | C(Cl)Cl | null | 16 | CCCCCCCCCCCCOc1ccc(C)nc1/C=C/CC(=O)O.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>CCCCCCCCCCCCOc1ccc(C)[n+]([O-])c1C=CCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-acb63839ed254e6a8aed9cc1fae732f3 | CCCCCCCCCCCCOc1ccc(CO)nc1/C=C/CC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCCOc1ccc(CCl)nc1/C=C/CC(=O)O.Cl | C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCCCCC)CO.S(=O)(Cl)Cl>>Cl.C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCCCCC)CCl | O[CH2:18][c:17]1[cH:16][cH:15][c:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:21](/[CH:22]=[CH:23]/[CH2:24][C:25](=[O:26])[OH:27])[n:20]1.O=S([Cl:19])[Cl:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:1... | CCCCCCCCCCCCOc1ccc(CO)nc1/C=C/CC(=O)O.O=S(Cl)Cl | CCCCCCCCCCCCOc1ccc(CCl)nc1/C=C/CC(=O)O.Cl | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccncc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]/[C:6]=[C:7].O=S(-[Cl;H0;D1;+0:8])-[Cl;H0;D1;+0:9]>>[C:7]=[C:6]/[c:5]:[#7;a:4]:[c:2](-[CH2;D2;+0:1]-[Cl;H0;D1;+0:8]):[c:3].[ClH;D0;+0:9] | null | [] | null | null | 30 | MINUTE | 2-(E-2-Carboxymethylethenyl)-3-dodecyloxy-6-(hydroxymethyl)pyridine (250 mg, 0.662 mmol) was dissolved in dry toluene (10 mL) under an argon atmosphere and cooled to 0∞C. Thionyl chloride (0.50 mL, 6.85 mmol) was slowly added and the solution was stirred at 0∞C for 30 minutes followed by 1 h at room temperature. The so... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccncc1 | Other | C1(=CC=CC=C1)C | null | 0.5 | CCCCCCCCCCCCOc1ccc(CO)nc1/C=C/CC(=O)O.O=S(Cl)Cl>C1(=CC=CC=C1)C>CCCCCCCCCCCCOc1ccc(CCl)nc1/C=C/CC(=O)O.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-de87afa26d714e14a6d512898b0c779c | CCCCC#CCCO>>C#CCCCCCCO | NCCCN.C(CC#CCCCC)O>>C(CCCCCC#C)O | [C:1]([CH2:2][CH2:3][CH2:4][CH3:5])#[C:6][CH2:7][CH2:8][OH:9]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9] | CCCCC#CCCO | C#CCCCCCCO | null | null | CCCCCC | Functional Group Interconversion | OtherReaction | 717941f395a910361dbd079f0406c8739db3d600df9659ab84f995c3dd1e77a5 | f5163dfbf670ee9f38d1be788eef0e0a983df5868f48fe01d48741d6a3f98157 | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[CH2;D2;+0:5]-[C:6]-[C:7]-[CH3;D1;+0:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:8]-[C:7]-[C:6]-[C;H0;D2;+0:5]#[CH;D1;+0:4] | null | [] | null | null | null | null | 35% KH in mineral oil (27 g, 240 mmol) under an argon atmosphere was washed with hexane and treated dropwise with 1,3-diaminopropane. The mixture was stirred at room temperature until it became homogeneous. The flask was cooled to 0° C. and 3-octyn-1-ol (10 g, 79 mmol, Lancaster Synthesis) was slowly added. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | null | null | null | null | CCCCCC | null | null | CCCCC#CCCO>CCCCCC>C#CCCCCCCO |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7742a39a60834848b33785d0d4bed03d | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1>>COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 | C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)C.C1=CC(=CC(=C1)Cl)C(=O)OO>>C(=O)(O)C/C=C/C1=[N+](C(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)C)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][c:16]2[cH:17][cH:18][c:19]([CH3:20])[n:21][c:23]2/[CH:24]=[CH:25]/[CH2:26][C:27](=[O:28])[OH:29])[cH:30][cH:31]1.O=C(O[OH:22])c1cccc(Cl)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH... | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1 | COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc(CCCCCCCCOc2ccc[nH+]c2)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13] | null | [] | 0 | CELSIUS | 15 | HOUR | 2-(E-2-Carboxymethylethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-methylpyridine (17.1 g, 41.5 mmol) was dissolved in dry CH2Cl2 (105 mL) and cooled to 0° C.; 50% mCPBA (15.8 g, 45.8 mmol) was added in three portions over 10 minutes. The cooling bath was removed and the reaction was stirred for 15 hours at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | c1ccccc1.C1=CC=[NH+]C=C1 | HCl | C(Cl)Cl | 0 | 15 | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3e00061d05f742f89b585d9476b78f3c | CC(C)(C)NC(=O)Oc1cccc(N)c1.COc1ccc(CCCCCCCCOc2ccc(CO)nc2/C=C/CC(=O)O)cc1>>CC(C)(C)NC(=O)O.COc1ccc(CCCCCCCCOc2ccc(COc3cccc(N)c3)nc2/C=C/CC(=O)O)cc1 | C(C)(C)(C)NC(=O)OC1=CC(=CC=C1)N.C(=O)([O-])[O-].[Cs+].[Cs+].O=S(Cl)Cl.C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)CO>>C(C)(C)(C)NC(O)=O.C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)COC1=CC(=CC=C1)N | [CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[O:8][c:30]1[cH:31][cH:32][cH:33][c:34]([NH2:35])[cH:36]1.[CH3:9][O:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][c:24]2[cH:25][cH:26][c:27]([CH2:28][OH:29])[n:37][c:38]2/[CH:39]=[CH:40]/[CH2:41][C:42](=[O:43])[OH:4... | CC(C)(C)NC(=O)Oc1cccc(N)c1.COc1ccc(CCCCCCCCOc2ccc(CO)nc2/C=C/CC(=O)O)cc1 | CC(C)(C)NC(=O)O.COc1ccc(CCCCCCCCOc2ccc(COc3cccc(N)c3)nc2/C=C/CC(=O)O)cc1 | null | null | C1(=CC=CC=C1)C.CN(C)C=O.CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d84570006c9b06d61a90671d4ae35783edb3aeb8aadae4f562c0552e7a1d0e47 | 23759678be0752f34d6a1080af185cb7d45ffa959fa58420ddb3fd04f32c824f | c1ccc(CCCCCCCCOc2ccc(COc3ccccc3)nc2)cc1 | [#7;a:1]:[c:2]-[C:3]-[OH;D1;+0:4].[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#7;a:1]:[c:2]-[C:3]-[O;H0;D2;+0:4]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9] | null | [] | null | null | 2 | HOUR | To a cooled (0° C.) solution of SOCl2 (0.51 mL, 7.0 mmol) in dry toluene (2 mL) under an argon atmosphere was added a solution of 2-(E-2-carboxymethylethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-hydroxymethylpyridine (300 mg, 0.70 mmol) in toluene (5 mL). After 5 minutes the cooling bath was removed and the reaction was ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary alcohol | Carbamic acid.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1.c1ccccc1 | null | C1(=CC=CC=C1)C.CN(C)C=O.CCOC(=O)C | null | 2 | CC(C)(C)NC(=O)Oc1cccc(N)c1.COc1ccc(CCCCCCCCOc2ccc(CO)nc2/C=C/CC(=O)O)cc1>C1(=CC=CC=C1)C.CN(C)C=O.CCOC(=O)C>CC(C)(C)NC(=O)O.COc1ccc(CCCCCCCCOc2ccc(COc3cccc(N)c3)nc2/C=C/CC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1cd2b443bf0f40aab875f1dc59222d5e | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1>>COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 | C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)C.ClC1=CC(=CC=C1)C(=O)OO>>C(=O)(O)C/C=C/C1=[N+](C(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)C)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][c:16]2[cH:17][cH:18][c:19]([CH3:20])[n:21][c:23]2/[CH:24]=[CH:25]/[CH2:26][C:27](=[O:28])[OH:29])[cH:30][cH:31]1.O=C(O[OH:22])c1cccc(Cl)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH... | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1 | COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc(CCCCCCCCOc2ccc[nH+]c2)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13] | null | [] | 0 | CELSIUS | 15 | HOUR | 2-(E-2-Carboxymethyl-ethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-methylpyridine (17.1 g, 41.5 mmol) was dissolved in dry CH2Cl2 (105 mL) and cooled to 0° C.; 50% m-chlorperbenzoic acid (15.8 g, 45.8 mmol) was added in three portions over 10 minutes. The cooling bath was removed and the reaction was stirred for 15 hours ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | c1ccccc1.C1=CC=[NH+]C=C1 | HCl | C(Cl)Cl | 0 | 15 | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b73d414da4b240d6b5789cafe3ba76e0 | COC(=O)c1cccc(CBr)c1.NC(N)=S>>COC(=O)c1cccc(CS)c1 | BrCC=1C=C(C(=O)OC)C=CC1.NC(=S)N>>SCC=1C=C(C(=O)OC)C=CC1 | Br[CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:12]1.NC(N)=[S:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][SH:11])[cH:12]1 | COC(=O)c1cccc(CBr)c1.NC(N)=S | COC(=O)c1cccc(CS)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].N-C(-N)=[S;H0;D1;+0:5]>>[SH;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | DAY | To a solution of methyl 3-bromomethylbenzoate (6.9 g, 30 mmol; Lancaster) in dry acetone (10 mL) was added via dropwise addition a solution of thiourea (2.28 g, 30 mmol) in dry acetone (40 mL) at room temperature. After 15 minutes the precipitated thiouronium salt was collected by filtration; the solids were washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | c1ccccc1 | HBr | CC(=O)C | null | 48 | COC(=O)c1cccc(CBr)c1.NC(N)=S>CC(=O)C>COC(=O)c1cccc(CS)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e195cd22266641658c299517b6bb6306 | COc1ccc(CCCCCCCCOc2ccc(CO)nc2/C=C/CC(=O)O)cc1>>COc1ccc(CCCCCCCCOc2ccc(CO)nc2CCCC(=O)O)cc1 | C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)CO>>C(=O)(O)CCCC1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)CO | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][c:16]2[cH:17][cH:18][c:19]([CH2:20][OH:21])[n:22][c:23]2/[CH:24]=[CH:25]/[CH2:26][C:27](=[O:28])[OH:29])[cH:30][cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:1... | COc1ccc(CCCCCCCCOc2ccc(CO)nc2/C=C/CC(=O)O)cc1 | COc1ccc(CCCCCCCCOc2ccc(CO)nc2CCCC(=O)O)cc1 | null | null | CO.C(Cl)Cl | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CCCCCCCCOc2cccnc2)cc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]/[CH;D2;+0:5]=[CH;D2;+0:6]/[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10] | null | [] | null | null | 5 | HOUR | 2-(E-2-Carboxymethyl-ethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-hydroxymethylpyridine (300 mg, 0.702 mmol) was dissolved in MeOH (3 mL) and treated with 5% Pd--C catalyst (30 mg). The reaction was stirred under an atmosphere of H2 (balloon pressure) for 5 hours. The reaction was diluted with CH2Cl2, and filtered throug... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccncc1 | null | CO.C(Cl)Cl | null | 5 | COc1ccc(CCCCCCCCOc2ccc(CO)nc2/C=C/CC(=O)O)cc1>CO.C(Cl)Cl>COc1ccc(CCCCCCCCOc2ccc(CO)nc2CCCC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2519da1cd5e64868a90adce0f029db99 | BrBr.c1ccc2sccc2c1>>Brc1csc2ccccc12 | BrBr.S1C2=C(C(=C1)C(=O)C1CCN(CC1)C(=O)OC(C)(C)C)C=CC=C2.S1C2=C(C=C1)C=CC=C2>>BrC=1C2=C(SC1)C=CC=C2 | Br[Br:1].[cH:2]1[cH:3][s:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>>[Br:1][c:2]1[cH:3][s:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | BrBr.c1ccc2sccc2c1 | Brc1csc2ccccc12 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 5c1f8d8eedabc10ba6c1fab933c953737f657e2a2bac2da17e7b3485129afe96 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2sccc2c1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]1:[#16;a:4]:[c:5]:[cH;D2;+0:6]:[c:7]:1:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[c:5]:[#16;a:4]:[c:3](:[c:2]):[c:7]:1:[c:8] | 48 | [{"value": 48.0, "product": "BrC=1C2=C(SC1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-[(Benzo[b]thiophene-3-yl)carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester ##STR13## Dissolve benzo[b]thiophene (23 g, 0.170 mmol) in carbon tetrachloride (80 mL). Add, by dropwise addition, a solution of bromine (26.85 g, 0.168 mmol) in carbon tetrachloride (30 mL) and stir at room temperature for 2 day... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2sccc2c1 | c1ccc2sccc2c1 | c1ccc2sccc2c1 | HBr | C(Cl)(Cl)(Cl)Cl | null | null | BrBr.c1ccc2sccc2c1>C(Cl)(Cl)(Cl)Cl>Brc1csc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b55a5b56ecd6472eb1f52e0aa86fe4a7 | COC(=O)c1ccc(OCCCCl)cc1.[I-]>>COC(=O)c1ccc(OCCCI)cc1 | S1C(=NC2=C1C=CC=C2)C(=O)C2CCN(CC2)CCCOC2=CC=C(C(=O)OC)C=C2.ClCCCOC1=CC=C(C(=O)OC)C=C1.[I-].[Na+]>>ICCCOC1=CC=C(C(=O)OC)C=C1 | Cl[CH2:12][CH2:11][CH2:10][O:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15][cH:14]1.[I-:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][I:13])[cH:14][cH:15]1 | COC(=O)c1ccc(OCCCCl)cc1.[I-] | COC(=O)c1ccc(OCCCI)cc1 | null | null | CC(=O)C.C(C)OCC | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[I-;H0;D0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:4] | null | [] | null | null | null | null | 4-[3-[4-[(2-Benzothiazolyl)carbonyl]-1-piperidinyl]propoxy]benzoic acid, methyl ester ##STR22## Dissolve 4-(3-chloropropoxy)benzoic acid, methyl ester (6.97 g, 30.5 mmol) in anhydrous acetone (100 mL) and add powdered sodium iodide (16.0 g, 107 mmol). Heat at reflux under an argon atmosphere for 38 hours. Dilute with e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccccc1 | Other | CC(=O)C.C(C)OCC | null | null | COC(=O)c1ccc(OCCCCl)cc1.[I-]>CC(=O)C.C(C)OCC>COC(=O)c1ccc(OCCCI)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ddb7a82add004633814f403a0639beca | Br.Nc1nc2c(Cl)cccc2s1>>Clc1cccc2sc(Br)nc12 | NC=1SC2=C(N1)C(=CC=C2)Cl.N(=O)[O-].[Na+].Br.Br>>BrC=1SC2=C(N1)C(=CC=C2)Cl | [BrH:9].N[c:8]1[s:7][c:6]2[cH:5][cH:4][cH:3][c:2]([Cl:1])[c:11]2[n:10]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[s:7][c:8]([Br:9])[n:10][c:11]12 | Br.Nc1nc2c(Cl)cccc2s1 | Clc1cccc2sc(Br)nc12 | null | [Cu]Br | O | Miscellaneous | OtherReaction | 71794c41e9e34c59e54f72d2d4e2a5da760ee16a1c6392802d18a408ac4e63ad | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2scnc2c1 | N-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[BrH;D0;+0:6]>>[Br;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | null | [] | 0 | CELSIUS | 15 | MINUTE | [(2-(4-Chlorobenzothiazotyl))carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester ##STR29## Slurry 2-amino-4-chlorobenzothiazole (0.255 mol) in water (325 mL), heat to reflux and add 48% hydrobromic acid (130 mL). Maintain at reflux for 20 minutes, cool to 0° C. and add a solution of sodium nitrite (17.56 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [Cu]Br.O | 0 | 0.25 | Br.Nc1nc2c(Cl)cccc2s1>[Cu]Br.O>Clc1cccc2sc(Br)nc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c442cb7f99a64365b3e5f35265fe51ee | Br.COc1ccc2nc(N)sc2c1>>COc1ccc2nc(Br)sc2c1 | NC=1SC2=C(N1)C=CC(=C2)OC.N(=O)[O-].[Na+].Br.Br>>BrC=1SC2=C(N1)C=CC(=C2)OC | [BrH:9].N[c:8]1[n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:12][c:11]2[s:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([Br:9])[s:10][c:11]2[cH:12]1 | Br.COc1ccc2nc(N)sc2c1 | COc1ccc2nc(Br)sc2c1 | null | [Cu]Br | O | Miscellaneous | OtherReaction | 71794c41e9e34c59e54f72d2d4e2a5da760ee16a1c6392802d18a408ac4e63ad | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2scnc2c1 | N-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[BrH;D0;+0:6]>>[Br;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | null | [] | 0 | CELSIUS | 15 | MINUTE | [(2-(6-Methoxybenzothiazolyl))carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester ##STR32## Slurry 2-amino-6-methoxybenzothiazole (0.255 mol) in water (325 mL), heat to reflux and add 48% hydrobromic acid (130 mL). Maintain at reflux for 20 minutes, cool to 0° C. and add a solution of sodium nitrite (17.56 g... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [Cu]Br.O | 0 | 0.25 | Br.COc1ccc2nc(N)sc2c1>[Cu]Br.O>COc1ccc2nc(Br)sc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a95ded096cae4bbf9c080ff7fbd1172e | Br.Nc1nc2ccc(F)cc2s1>>Fc1ccc2nc(Br)sc2c1 | NC=1SC2=C(N1)C=CC(=C2)F.N(=O)[O-].[Na+].Br.Br>>BrC=1SC2=C(N1)C=CC(=C2)F | [BrH:8].N[c:7]1[n:6][c:5]2[cH:4][cH:3][c:2]([F:1])[cH:11][c:10]2[s:9]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([Br:8])[s:9][c:10]2[cH:11]1 | Br.Nc1nc2ccc(F)cc2s1 | Fc1ccc2nc(Br)sc2c1 | null | [Cu]Br | O | Miscellaneous | OtherReaction | 71794c41e9e34c59e54f72d2d4e2a5da760ee16a1c6392802d18a408ac4e63ad | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2scnc2c1 | N-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[BrH;D0;+0:6]>>[Br;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | null | [] | 0 | CELSIUS | 15 | MINUTE | [(2-(6-Fluorobenzothiazolyl))carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester ##STR36## Slurry 2-amino-6-fluorobenzothiazole (0.255 mol) in water (325 mL), heat to reflux and add 48% hydrobromic acid (130 mL). Maintain at reflux for 20 minutes, cool to 0° C. and add a solution of sodium nitrite (17.56 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [Cu]Br.O | 0 | 0.25 | Br.Nc1nc2ccc(F)cc2s1>[Cu]Br.O>Fc1ccc2nc(Br)sc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6226c54c8fa747adb5ea37610f0dc1ec | CCCCCCCCCCBr.Cc1ncc[nH]1>>CCCCCCCCCCn1ccnc1C | CC=1NC=CN1.BrCCCCCCCCCC.[OH-].[Na+]>>C(CCCCCCCCC)N1C(=NC=C1)C | Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[nH:11]1[cH:12][cH:13][n:14][c:15]1[CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][n:14][c:15]1[CH3:16] | CCCCCCCCCCBr.Cc1ncc[nH]1 | CCCCCCCCCCn1ccnc1C | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5118ce9eea46859cccf16d01cf8151757afd816de0c93fe6fcb74a0ee15c5a67 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1c[nH]cn1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[nH;D2;+0:9]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[c:7]:[#7;a:6]:[c:5]:1-[C;D1;H3:4] | null | [] | 65 | CELSIUS | 3 | HOUR | A mixture of 2-methylimidazole (12.3 g; 0.15 mol), 1-bromodecane (33.15 g; 0.15 mol), sodium hydroxide solution (69.5 ml. of 11.5M solution; 0.8 mol) and tetra-n-butylammonium bromide (1.95 g; 0.006 mol) in toluene (300 ml) was stirred rapidly for 3 hours at 65° C. After cooling to between 20° and 25° C., the toluene l... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1 | HBr | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C | 65 | 3 | CCCCCCCCCCBr.Cc1ncc[nH]1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>CCCCCCCCCCn1ccnc1C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-93dd2a57937143018e7246596ef88f0f | CCCCCCCCCCBr.Cc1n[nH]c(C)n1>>CCCCCCCCCCn1nc(C)nc1C | CC1=NNC(=N1)C.BrCCCCCCCCCC.[OH-].[Na+]>>C(CCCCCCCCC)N1N=C(N=C1C)C | Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[nH:11]1[n:12][c:13]([CH3:14])[n:15][c:16]1[CH3:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][n:11]1[n:12][c:13]([CH3:14])[n:15][c:16]1[CH3:17] | CCCCCCCCCCBr.Cc1n[nH]c(C)n1 | CCCCCCCCCCn1nc(C)nc1C | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9f47013937e839adceb07b7e24945feef9d8519d2c1c97fb8023b4a65c36ed06 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1nc[nH]n1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:1-[C;D1;H3:4] | null | [] | 120 | CELSIUS | null | null | A mixture of 3,5-dimethyl-1,2,4-triazole (6.0 parts; 0.062 mol ex (b) above) and 1-bromodecane (14.4 parts; 0.065 mol) in dimethylformamide (16 ml) was heated together at 120° C. for 23 hours. The cooled reaction mixture was diluted with water (100 ml), a solution of sodium hydroxide (2.62 parts; 0.065 mol) in water (1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nc[nH]n1 | c1nc[nH]n1 | c1nc[nH]n1 | HBr | O.CN(C=O)C | 120 | null | CCCCCCCCCCBr.Cc1n[nH]c(C)n1>O.CN(C=O)C>CCCCCCCCCCn1nc(C)nc1C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a1bd64920c2540e2b27d5dc83fe97a0e | COc1ccc(CCN)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>COc1ccc(CCN=C=O)cc1 | COC1=CC=C(C=C1)CCN.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>COC1=CC=C(C=C1)CCN=C=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH2:9])[cH:12][cH:13]1.ClC(Cl)(Cl)O[C:10](OC(Cl)(Cl)Cl)=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]=[C:10]=[O:11])[cH:12][cH:13]1 | COc1ccc(CCN)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | COc1ccc(CCN=C=O)cc1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 38334b31448e1d8428e2cb6569eceaecc2305b2359c734a98433aa0746ff9140 | a539b8d5e65abe163774733461d6850ba8234d38df1df3c2ccdeef5ce9de389b | c1ccccc1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[N;H0;D2;+0:5]=[C;H0;D2;+0:1]=[O;D1;H0:2] | 62.1 | [{"value": 62.1, "product": "COC1=CC=C(C=C1)CCN=C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.53 g (30 mmol) of 4-methoxy-β-phenylethylamine are added dropwise to a solution of 2.96 g (10.0 mmol) of triphosgene in 30 ml of dry tetrahydrofuran and the mixture is heated at the boiling point for 2 hours. The solution is cooled to room temperature and filtered and the filtrate is concentrated in vacuo. The colorl... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Primary amine | Isocyanate | null | null | c1ccccc1 | HCl | O1CCCC1 | null | null | COc1ccc(CCN)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O1CCCC1>COc1ccc(CCN=C=O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7820dc9305b04fb08a858045efcb9faa | O=C1CN2CCC1CC2.O=Cc1ccc(Cl)cc1>>O=C1C(=Cc2ccc(Cl)cc2)N2CCC1CC2 | O.N12CC(C(CC1)CC2)=O.ClC1=CC=C(C=O)C=C1.[OH-].[Na+]>>ClC1=CC=C(C=C2N3CCC(C2=O)CC3)C=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][c:8]([Cl:9])[cH:10][cH:11]1>>[O:1]=[C:2]1[C:3](=[CH:4][c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[N:12]2[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]2 | O=C1CN2CCC1CC2.O=Cc1ccc(Cl)cc1 | O=C1C(=Cc2ccc(Cl)cc2)N2CCC1CC2 | null | null | C(C)O | 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] | 79.9 | [{"value": 76.0, "product": "ClC1=CC=C(C=C2N3CCC(C2=O)CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "ClC1=CC=C(C=C2N3CCC(C2=O)CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | A solution of 3-quinuclidinone (54.5 g), 4-chlorobenzaldehyde (84.0 g) and sodium hydroxide (3.50 g) in absolute ethanol (400 cm3) was heated at reflux for 2.5 hours. The mixture was cooled and addition of water (100 cm3) caused the product to precipitate as an orange solid. The precipitate was collected and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Enamine | C1CN2CCC1CC2 | C1CN2CCC1CC2 | c1ccccc1.C1CN2CCC1CC2 | HO- | C(C)O | null | 48 | O=C1CN2CCC1CC2.O=Cc1ccc(Cl)cc1>C(C)O>O=C1C(=Cc2ccc(Cl)cc2)N2CCC1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-655469847fac40a7af406d5af77d87ac | NN.O=C1C(=Cc2ccc(Cl)cc2)N2CCC1CC2>>Clc1ccc(-c2cc(C3CCNCC3)n[nH]2)cc1 | ClC1=CC=C(C=C2N3CCC(C2=O)CC3)C=C1.[OH-].[K+].O.NN>>N1CCC(CC1)C1=NNC(=C1)C1=CC=C(C=C1)Cl | [NH2:15][NH2:16].O=[C:8]1[C:7](=[CH:6][c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:18][cH:17]2)[N:12]2[CH2:11][CH2:10][CH:9]1[CH2:14][CH2:13]2>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[n:15][nH:16]2)[cH:17][cH:18]1 | NN.O=C1C(=Cc2ccc(Cl)cc2)N2CCC1CC2 | Clc1ccc(-c2cc(C3CCNCC3)n[nH]2)cc1 | null | null | C(CO)O | Miscellaneous | OtherReaction | 1c95fac55fdd7347a24b2ce4d60f33d06049a4856c1bf1042a8118991f0a857c | 7970252e4561f606c947a16ca04ebcf9b03b0be6e011259e43787943a2f957da | c1ccc(-c2cc(C3CCNCC3)n[nH]2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]2-[C:3]-[C:4]-[N;H0;D3;+0:5](-[C:6]-[C:7]-2)-[C;H0;D3;+0:8]-1=[CH;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[NH2;D1;+0:15]-[NH2;D1;+0:16]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:9]1:[cH;D2;+0:8]:[c;H0;D3;+0:1](-[C:2]2-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-2):[n;H0;D2;+0:15]:[nH;D2... | 85 | [{"value": 85.0, "product": "N1CCC(CC1)C1=NNC(=C1)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | A mixture of 2-(4-chlorobenzylidene)quinuclidin-3-one (35.0 g), potassium hydroxide (15.0 g) and hydrazine hydrate (11.0 cm3) in ethylene glycol(100 cm3) was heated at 110° C. for 15 minutes to produce a dear, dark brown solution. Hydrazine hydrate and water were distilled from the solution over 1 hour at 110° C. to 19... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Hydrazine.Ketone | Secondary amine | C1CN2CCC1CC2 | c1cn[nH]c1.C1CCNCC1 | c1ccccc1.c1cn[nH]c1.C1CCNCC1 | HO- | C(CO)O | 110 | null | NN.O=C1C(=Cc2ccc(Cl)cc2)N2CCC1CC2>C(CO)O>Clc1ccc(-c2cc(C3CCNCC3)n[nH]2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5ad50fb1ab9048b7b363963e9f02dabf | ClCc1ccc(Cl)cc1.Clc1ccc(-c2cc(C3CCNCC3)n[nH]2)cc1>>Clc1ccc(CN2CCC(c3cc(-c4ccc(Cl)cc4)[nH]n3)CC2)cc1 | N1CCC(CC1)C1=NNC(=C1)C1=CC=C(C=C1)Cl.C(C)N(CC)CC.ClC1=CC=C(CCl)C=C1>>ClC1=CC=C(CN2CCC(CC2)C2=NNC(=C2)C2=CC=C(C=C2)Cl)C=C1 | Cl[CH2:6][c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:26][cH:25]1.[NH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]3)[nH:21][n:22]2)[CH2:23][CH2:24]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH:10]([c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][c:17]([Cl:18])[cH:... | ClCc1ccc(Cl)cc1.Clc1ccc(-c2cc(C3CCNCC3)n[nH]2)cc1 | Clc1ccc(CN2CCC(c3cc(-c4ccc(Cl)cc4)[nH]n3)CC2)cc1 | null | null | ClCCl.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCC(c3cc(-c4ccccc4)[nH]n3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | 26 | [{"value": 26.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(4-piperidinyl)-5-(4-chlorophenyl)pyrazole (1.50 g), triethylamine (1.60 cm3) and 4-chlorobenzyl chloride (0.92 g) in 3:1 dichloromethane-dimethylformamide (20 cm3) was stirred at room temperature for 4.5 hours. Dichloromethane was removed by evaporation and the crude product was partitioned between wat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1cn[nH]c1.c1ccccc1 | HCl | ClCCl.CN(C=O)C | null | null | ClCc1ccc(Cl)cc1.Clc1ccc(-c2cc(C3CCNCC3)n[nH]2)cc1>ClCCl.CN(C=O)C>Clc1ccc(CN2CCC(c3cc(-c4ccc(Cl)cc4)[nH]n3)CC2)cc1 |
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