Trichloroacetyl chloride → 2,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methoxybenzoyl)phenyl]-acetamide

HRID 1788050Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)=[O:19].[Cl:27][C:28]([Cl:33])([Cl:32])[C:29](Cl)=[O:30].C(N(CC)CC)C>C(Cl)Cl>[Cl:27][C:28]([Cl:33])([Cl:32])[C:29]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18](=[O:19])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)=[O:30]

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of intermediate 11 (0.0536 mol) in DCM (200 ml) was cooled to 5° C. under N2 flow. A solution of trichloro-acetylchloride (0.0643 mol) was added dropwise at 5° C. The mixture was stirred at 5° C. for 30 minutes. A solution of triethylamine (0.0643 mol) was added dropwise at 5° C. The mixture was stirred at 5° C. for 1 hour then at room temperature for 2 hours, poured out into ice water and extracted with DCM. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated, yielding 27.4 g (quantitative) of 2,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methoxybenzoyl)phenyl]-acetamide (intermediate 12).

Workup

stirringThe mixture was stirred at 5° C. for 1 hour
waitat room temperature for 2 hours
extractionextracted with DCM
customThe organic layer was separated
washwashed with water
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-cc951cb177d4449cbb7983bb42eb8ee5
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511138B2

Reaction notes

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