Thiourea → Methyl 2-amino-4-cyclopropyl-1,3-thiazole-5-carboxylate hydrobromide

HRID 389104Notes

Reaction equation

HRID 389104 reaction equation
[Br:1][CH:2]([C:7]([CH:9]1[CH2:11][CH2:10]1)=O)[C:3]([O:5][CH3:6])=[O:4].[NH2:12][C:13]([NH2:15])=[S:14]>C(O)C>[BrH:1].[NH2:15][C:13]1[S:14][C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:7]([CH:9]2[CH2:11][CH2:10]2)[N:12]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58243876Methyl 2-bromo-3-cyclopropyl-3-oxopropanoate

Product 1

HCID 86653012Methyl 2-amino-4-cyclopropyl-1,3-thiazole-5-carboxylate hydrobromideYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 2-bromo-3-cyclopropyl-3-oxopropanoate (3.3 g) and thiourea (900 mg) were dissolved in ethanol (20 ml) followed by stirring at 80° C. overnight. After cooling to room temperature, the solvent was evaporated under reduced pressure, and the residue was washed with isopropanol to obtain, as a grayish white solid, methyl 2-amino-4-cyclopropyl-1,3-thiazole-5-carboxylate monohydrobromide (2.82 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. washthe residue was washed with isopropanol

Sources & evidence

ORD record
ord-a49b409e4d3f46b592b90b530e6029cf
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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