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

HRID 1788042Notes

Reaction equation

[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)=[O:25].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]([Cl:7])([Cl:6])[C:3]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[C:24](=[O:25])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)=[O:4]

Participants

Conditions

Temperature: 5 °C

Procedure

Trichloro-acetylchloride (0.0848 mol) was added dropwise at 5° C. to a mixture of intermediate 3 (0.0707 mol) in DCM (250 ml) under N2 flow. The mixture was stirred at 5° C. for 30 minutes. Triethylamine (0.0848 mol) was added dropwise at 5° C. The mixture was stirred at 5° C. for 1 hour, then at room temperature for 2 hours and poured out into ice water. DCM was added. The mixture was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from diethyl ether/DIPE. The precipitate was filtered off and dried, yielding 33.7 g (95%) of 2,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-fluorobenzoyl)phenyl]-acetamide (intermediate 4).

Workup

stirringThe mixture was stirred at 5° C. for 1 hour
waitat room temperature for 2 hours
extractionThe mixture was extracted with DCM
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent was evaporated
customThe residue was crystallized from diethyl ether/DIPE
filtrationThe precipitate was filtered off
customdried

Sources & evidence

ORD record: ord-03857d6b9804438ab847be67069e97ee
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511138B2

Reaction notes

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