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

HRID 1039147노트

반응식

HRID 1039147 반응식
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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 887Methanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-c7f894d5d3564aac93e3d5aee3c60438
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552039B2

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