Methanethioamide → 4-(2-Methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 1776157Notes

Reaction equation

HRID 1776157 reaction equation
[CH:1]([NH2:3])=[S:2].[CH2:4]([O:6][C:7](=[O:20])[CH:8](Br)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=O)[CH3:5]>CCO>[CH2:4]([O:6][C:7]([C:8]1[S:2][CH:1]=[N:3][C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=[O:20])[CH3:5]

Participants

4

Reactant 2

HCID 3005587MethanethioamideHCID 580160512-Bromo-3-(2-methoxyphenyl)-3-oxo-propionic acid ethyl ester

Product 1

HCID 670764344-(2-Methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a 0° C. solution of thioformamide (prepared according to Eur. J. Med. Chem. 2004, 39, 867-872) (0.70 g, 11.5 mmol) in absolute EtOH (1 ml) was added a solution of 2-bromo-3-(2-methoxyphenyl)-3-oxo-propionic acid ethyl ester (2.4 g, 7.97 mmol) in ethanol abs. (9 ml) in drops. The reaction mixture was stirred at room temperature for 72 hours. After quenching with water and extraction with chloroform, the organics were dried over Na2SO4 and evaporated. Flash chromatography on SiO2 gel (petroleum ether/ethyl acetate, 60/40) gave crude 4-(2-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester that was used in the next step without further purification.

Workup

  1. customAfter quenching with water and extraction with chloroform
  2. dry with materialthe organics were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-5c7193ff01834c569da1cd243b3e6cee
Source dataset
uspto-grants-2016_02
Patent number
US09265769B2

Reaction notes

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