Dimethylformamide → N-(2-phenylethyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole-2-amine

HRID 732186

Reaction equation

HRID 732186 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)=O.CN(C)C=O>O>[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[S:11][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 735845(2-Phenylethyl)thiourea

Product 1

HCID 23143279N-(2-phenylethyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole-2-amineYield 74.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(2-phenylethyl)thiourea (3.60 g, 20 mmol), 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone (5.34 g, 20 mmol) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 16 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained solid was washed with hexane to give the title compound (5.2 g, yield 74%) as pale-yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-d58ea20db5c04fb18522880356d2f28b
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Linked notes

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