Triethylamine → HCID 10810822, compound

HRID 395738Notes

Reaction equation

HRID 395738 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[C:6]([NH:8][C:9]1[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:7])#[N:2].C(N(CC)CC)C.[C:26]([C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[C:6]([NH:8][C:9]1[C:10]([NH:15][C:34](=[O:35])[C:33]2[CH:37]=[CH:38][C:30]([C:26]([CH3:28])([CH3:27])[CH3:29])=[CH:31][CH:32]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chlorideHCID 10705025HCID 10705025, compound

Product 1

HCID 10810822HCID 10810822, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N1-(3-cyanobenzoyl)-1,2-benzenediamine (500 mg, 2.1 mmol), triethylamine (0.44 mL, 3.2 mmol) in methylene chloride (100 mL) was added 4-tert-butylbenzoyl chloride (0.41 mL, 2.1 mmol). After stirring for 20 hours, the reaction mixture was concentrated in vacuo. Chromatography (silica gel, 20% ethyl acetate/80% hexanes) yielded 730 mg (87%) of the title compound as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-dfee334c567641cb9706c21b9261d886
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

Loading…