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

HRID 732195

Reaction equation

HRID 732195 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 74%

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) and 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 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 74%) as pale-yellow crystals.

Workup

  1. extractionextracted 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-024d07fd5d9f4ba3ab58868d34764847
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Linked notes

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