Ethyl bromopyruvate → Ethyl 2-aminothiazole-4-carboxylate hydrobromide
Reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[Br:5][CH2:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)C>[BrH:5].[NH2:1][C:2]1[S:3][CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
To a stirring suspension of thiourea (6.0 g, 78.8 mmol) in ethanol (80 mL) was added ethyl bromopyruvate (15.4 g, 78.8 mmol). The resulting solution was heated at 45° C. for 23 h. The solution was cooled at 0° C. for 24 h, and the crystals were collected by filtration and washed with cold ethanol to provide the title compound (15.8 g, 79%). 1H NMR (400 MHz, CD3OD) δ 7.70 (s, 1H), 4.41 (q, 2H), 1.38 (t, 3H).
Workup
- temperatureThe solution was cooled at 0° C. for 24 h
- filtrationthe crystals were collected by filtration
- washwashed with cold ethanol
Sources & evidence
- ORD record
- ord-df89d477a2234d44ba4f8dcf7604ffb8
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562842B2
Reaction notes
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