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Pyridine → 2,2,2-trichloro-N-[3-chloro-4-(trifluoromethyl)phenyl]acetamide

HRID 603168
Notes
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Reaction equation

HRID 603168 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[C:4]([Cl:12])[CH:3]=1.N1C=CC=CC=1.[Cl:19][C:20]([Cl:25])([Cl:24])[C:21](Cl)=[O:22]>ClCCl>[Cl:19][C:20]([Cl:25])([Cl:24])[C:21]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[C:4]([Cl:12])[CH:3]=1)=[O:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 679623-Chloro-4-(trifluoromethyl)aniline

Product 1

HCID 576567882,2,2-trichloro-N-[3-chloro-4-(trifluoromethyl)phenyl]acetamideYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino-2-chlorobenzotrifluoride (300 mg) and pyridine (243 mg) in dichloromethane (10 mL) was added a solution of trichloroacetyl chloride (279 mg) in dichloromethane (5 mL) dropwise. The solution was stirred for 2 hrs and then concentrated at reduced pressure. The residue was purified by silica gel chromatography eluting with 0-10% ethyl acetate in hexane to give the title compound as a white solid (360 mg, 69%).

Workup

  1. concentrationconcentrated at reduced pressure
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with 0-10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ada302043cf441feab5994ff6e306249
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906645B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes