Trifluoroacetic acid → 2-amino-N,N-dimethyl-1,3-thiazole-4-carboxamide
Reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[O:17])[N:14]([CH3:16])[CH3:15])[N:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:15][N:14]([CH3:16])[C:13]([C:11]1[N:12]=[C:8]([NH2:7])[S:9][CH:10]=1)=[O:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of (4-dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester (150 mg, 0.53 mmol) in dichloromethane (1 mL) at 0° C. was added trifluoroacetic acid (2.5 mL, 32 mmol) and the mixture stirred at 0° C. until all of the starting material had been consumed. The reaction mixture was concentrated in vacuo, the residue dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate (2×), brine, dried over sodium sulfate and concentrated in vacuo to give crude 2-amino-thiazole-4-carboxylic acid dimethylamide as a viscous colorless oil which was used without further purification (85 mg, 90%).
Workup
- customhad been consumed
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutionthe residue dissolved in ethyl acetate
- washwashed with saturated aqueous sodium bicarbonate (2×), brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ab1f620ec28c40f18aa42485c2e4a7cb
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371869B2
Reaction notes
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