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

HRID 1443646

反応式

HRID 1443646 の反応式
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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-584223c4e5044fc29cf5192ebaf70216
出典データセット
uspto-grants-2010_02
特許番号
US07662771B2

関連ノート

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