Hydrochloric Acid → Methyl 5-bromo-2-methyl-1,3-thiazole-4-carboxylate

HRID 2244405Notes

Reaction equation

HRID 2244405 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]([OH:10])=[O:9].Cl.[CH3:12]O>CCOCC>[CH3:12][O:9][C:8]([C:3]1[N:4]=[C:5]([CH3:7])[S:6][C:2]=1[Br:1])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 451175845-Bromo-2-methyl-1,3-thiazole-4-carboxylic acid

Product 1

HCID 16427155Methyl 5-bromo-2-methyl-1,3-thiazole-4-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-bromo-2-methyl-thiazole-4-carboxylic acid (1.50 g, 6.75 mmol) in methanol (80.00 ml) was treated with a saturated solution of HCl in ether (3.00 ml). The reaction mixture was heated at reflux for 3 h then the volatiles were removed. The residue was purified by flash chromatography (methylene chloride/methanol) yielding 5-bromo-2-methyl-thiazole-4-carboxylic acid methyl ester (1.30 g, 82%) as a white solid, MS (ISP): m/e=235.9, 237.9 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. customthe volatiles were removed
  4. customThe residue was purified by flash chromatography (methylene chloride/methanol)

Sources & evidence

ORD record
ord-157b3d133e4446e08515daba6cc1b04c
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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