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

HRID 732168

Reaction equation

HRID 732168 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=O.[C:15]1([CH2:21][CH2:22][NH:23][C:24]([NH2:26])=[S:25])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN(C)C=O>O>[C:15]1([CH2:21][CH2:22][NH:23][C:24]2[S:25][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=3)[N:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromo-1-[4-(trifluoromethyl)phenyl]-ethanone (5.34 g), N-(2-phenylethyl)thiourea (3.60 g) and N,N-dimethylformamide (20 mL) was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated to give the title compound (5.20 g, yield 74%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ba9edc3cfea846ac9d61fddbdf795fc6
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Linked notes

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