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]>CCO>[BrH:5].[CH2:11]([O:10][C:8]([C:7]1[N:1]=[C:2]([NH2:4])[S:3][CH:6]=1)=[O:9])[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
To a stirred suspension of thiourea (24.26 g, 0.319 mol) in 200 proof EtOH (350 mL) at RT, under N2, ethyl bromopyruvate (62.16 g, 0.319 mol) was added dropwise. Upon completion the yellow solution was heated to 45° C. for 15 h, then placed in a fridge overnight. The precipitate was filtered off and washed with cold EtOH (3×100 mL) to yield the title compound as a pale yellow amorphous solid. MS m/z: 173.1 (M+H), 195.1 (M+Na). Calc'd. for C6H9BrN2O2S-253.12.
Workup
- filtrationThe precipitate was filtered off
- washwashed with cold EtOH (3×100 mL)
Sources & evidence
- ORD record
- ord-f5975fd286cc49ff8034f028dfb50512
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196104B2
Reaction notes
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