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

HRID 1400175Notes

Reaction equation

HRID 1400175 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-1e5a69bf5c1048e7a337288a698a538d
Source dataset
uspto-grants-2014_12
Patent number
US08906935B2

Reaction notes

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