4-Methoxybenzenecarbothioamide → HCID 59594764, compound

HRID 2263381Notes

Reaction equation

HRID 2263381 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][CH:4]=1.[CH2:12]([O:14][C:15](=[O:23])[CH:16](Cl)[C:17](=O)[CH:18]([F:20])[F:19])[CH3:13]>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[S:8][C:7]([C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:9][C:17]=1[CH:18]([F:20])[F:19])=[O:23])[CH3:13]

Participants

4

Reactant 2

HCID 7368274-MethoxybenzenecarbothioamideHCID 19391743HCID 19391743, compound

Product 1

HCID 59594764HCID 59594764, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

8.84 g 4-Methoxythiobenzamide were dissolved in 100 ml ethanol and warmed to 50° C. Then 10.59 g 2-chloro-4,4-difluoro-3-oxo-butyric acid ethyl ester were added and the reaction mixture stirred under reflux for three hours. The cooled reaction mixture was evaporated in vacuo and the residue purified by chromatograph on silica gel with the eluent ethyl acetate/petroleum benzene=1:4 to obtain 7.04 g 4-difluoromethyl-2-(4-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester as pale yellow solid.

Workup

  1. temperatureunder reflux for three hours
  2. customThe cooled reaction mixture
  3. customwas evaporated in vacuo
  4. customthe residue purified by chromatograph on silica gel with the eluent ethyl acetate/petroleum benzene=1:4

Sources & evidence

ORD record
ord-aa2dc76326a746e9b5aa542c02f29c6a
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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