Water → N-(3-Methylbutyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine

HRID 507997

Reaction equation

HRID 507997 reaction equation
[CH3:1][CH:2]([CH3:9])[CH2:3][CH2:4][NH:5][C:6]([NH2:8])=[S:7].Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=O.C([O-])(=O)C.[Na+].O>C(O)C>[CH3:1][CH:2]([CH3:9])[CH2:3][CH2:4][NH:5][C:6]1[S:7][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][CH:15]=2)[N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 517045Sodium AcetateHCID 2459097(3-Methyl-butyl)-thiourea

Product 1

HCID 23143261N-(3-Methylbutyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amineYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(3-methylbutyl)thiourea (3.00 g, 20.5 mmol), 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone (5.45 g, 20.5 mmol), sodium acetate (2.19 g, 26.7 mmol) in ethanol (50 mL) was stirred at 90° C. for 4 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 recrystallized from dichloromethane-hexane to give the title compound (1.76 g, yield 27%) 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. customThe obtained solid was recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-17451a31c1a242d2998f0b1a7f9c5bc1
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Linked notes

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