Thioacetimidic acid 2-(4-methoxyphenyl)-2-oxoethyl ester hydrobromide → 4-(4-Methoxy-phenyl)-2-methyl-thiazole

HRID 1616533

Reaction equation

HRID 1616533 reaction equation
Br.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][S:12][C:13](=[NH:15])[CH3:14])=[CH:6][CH:5]=1>CO.C([O-])(O)=O.[Na+].[Cl-].[Zn+2].[Cl-]>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:13]([CH3:14])[S:12][CH:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 68489019Thioacetimidic acid 2-(4-methoxyphenyl)-2-oxoethyl ester hydrobromide

Product 1

HCID 7687654-(4-Methoxy-phenyl)-2-methyl-thiazoleYield 92.4%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Heat a mixture of thioacetimidic acid 2-(4-methoxyphenyl)-2-oxoethyl ester hydrobromide (10.0 g, 32.9 mmol) and zinc (II) chloride (4.50 g, 33.0 mmol) in methanol (80 mL) at reflux under nitrogen protection for 6.5 hours. Cool the mixture, slowly dilute with saturated NaHCO3 (300 mL), and extract with methylene chloride (400 mL×2). Dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure. Purify the crude product by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (9:1), to provide 4-(4-methoxyphenyl)-2-methylthiazole (6.24 g, 92%): APCI mass spectrum m/z 206 [C11H11NOS+H]+.

Workup

  1. temperatureHeat
  2. temperatureat reflux under nitrogen protection for 6.5 hours
  3. temperatureCool the mixture
  4. extractionextract with methylene chloride (400 mL×2)
  5. dry with materialDry the combined organic extracts over sodium sulfate
  6. customremove the solvent under reduced pressure
  7. customPurify the crude product by flash column chromatography on silica gel
  8. washeluting with hexanes/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-a1bcfb00b9c04d91bda42a3dfa499caf
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Linked notes

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