Ethyl bromopyruvate → Ethyl 2-aminothiazole-4-carboxylate hydrobromide

HRID 460188Notes

Reaction equation

HRID 460188 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

HCID 66144Ethyl bromopyruvateHCID 2723790Thiourea

Product 1

HCID 16495520Ethyl 2-aminothiazole-4-carboxylate hydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. filtrationThe precipitate was filtered off
  2. 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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