3-Bromo-1,1,1-trifluoro-2-propanone → 2-Thiazolamine, 4-(trifluoromethyl)-

HRID 1642404Notes

Reaction equation

HRID 1642404 reaction equation
Br[CH2:2][C:3](=O)[C:4]([F:7])([F:6])[F:5].[NH2:9][C:10]([NH2:12])=[S:11]>C(O)C>[F:5][C:4]([F:7])([F:6])[C:3]1[N:9]=[C:10]([NH2:12])[S:11][CH:2]=1

Participants

4

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 2723790Thiourea

Product 1

HCID 12014172-Thiazolamine, 4-(trifluoromethyl)-Yield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-bromo-1,1,1-trifluoroacetone (5.0 g, 26.184 mmol) and thiourea (2.0 g, 26.184 mmol) in ethanol was heated to 50-55° C. for 2.0 h till TLC indicated completion of the reaction. The reaction mixture was concentrated and the residue made basic with 5% NaOH. The mixture was then extracted with ethyl acetate and concentrated to yield a residue which was column purified to afford 3.8 g of the desired compound: 1H NMR (300 MHz, DMSO-d6) δ 7.25 (s, 1H), 7.43 (br s, 2H); ESI-MS (m/z) 169.37 (M+H)+.

Workup

  1. customcompletion of the reaction
  2. concentrationThe reaction mixture was concentrated
  3. extractionThe mixture was then extracted with ethyl acetate
  4. concentrationconcentrated
  5. customto yield a residue which
  6. custompurified

Sources & evidence

ORD record
ord-3eec514a2863455f8c7ed5326fe01962
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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