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

HRID 2069106Notes

Reaction equation

HRID 2069106 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-5a95357f40e945e79e1e31d49d7d25bc
Source dataset
uspto-grants-2012_10
Patent number
US08299090B2

Reaction notes

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