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

HRID 1441469
Notes
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Reaction equation

HRID 1441469 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)=[O:18].[Cl:26][C:27]([Cl:32])([Cl:31])[C:28](Cl)=[O:29].C(N(CC)CC)C>C(Cl)Cl>[Cl:26][C:27]([Cl:32])([Cl:31])[C:28]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:17](=[O:18])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)=[O:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 17976111[2-Amino-5(4-methylbenzoyl)phenyl](3-chlorophenyl)-methanone

Product 1

HCID 686890442,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methylbenzoyl)phenyl]-acetamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

Intermediate 20 (0.0085 mol) was added at 5° C. to DCM (30 ml) under N2 flow, trichloro-acetyl chloride (0.01 mol) then triethylamine (0.01 mol) were added dropwise. The mixture was brought to room temperature, stirred at room temperature for 3 hours, poured out into ice water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated, yielding 4.2 g (quantitative) of 2,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methylbenzoyl)phenyl]-acetamide (intermediate 21).

Workup

  1. customwas brought to room temperature
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e94ecf34c8584c519d01302b00c13899
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07655654B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes