Hydrochloric Acid → Methyl 4-methanesulfonamidobenzoate

HRID 1612740

反応式

HRID 1612740 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].N1C=CC=CC=1.[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.Cl>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 12082Methyl 4-aminobenzoateHCID 31297Methanesulfonyl chloride

生成物 1

HCID 669159Methyl 4-methanesulfonamidobenzoate収率 95.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of methanesulfonyl chloride (15.2 g, 132 mmol) in methylene chloride (50 mL) was added dropwise to a stirring slurry of pyridine (41.8 g, 529 mmol) and methyl-4-aminobenzoate (20.0 g, 132 mmol) in methylene chloride (110 mL) cooled by a dry ice/acetone bath. The reaction mixture was allowed to warm to ambient temperature and was stirred overnight. The reaction mixture was added to 400 mL of 4% aqueous HCl solution and the solid that formed was collected by filtration. The orange solid was recrystallized from methanol to give 28.8 g (91.5%) of an orange-pink solid, mp 147°-150° C.

後処理

  1. temperaturecooled by a dry ice/acetone bath
  2. customthe solid that formed
  3. filtrationwas collected by filtration
  4. customThe orange solid was recrystallized from methanol

出典と根拠

ORDレコード
ord-8fbf37ba065b4942bedf0a48e778f423
出典データセット
uspto-grants-1993_03
特許番号
US05190953

関連ノート

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