p-Toluenesulfonic acid monohydrate → 2-(Chloromethyl)-1-phenyl-1H-benzimidazole

HRID 1284481

反応式

HRID 1284481 の反応式
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[Cl:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=1

参加物

5

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 14819969N-(2-Anilinophenyl)-2-chloroacetamide

生成物 1

HCID 202518962-(Chloromethyl)-1-phenyl-1H-benzimidazole収率 36.5%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of 2-chloro-N-(2-anilinophenyl)acetamide (10 g) and p-toluenesulfonic acid monohydrate (4.5 g) in benzene (250 ml) was refluxed for 1.5 hours under an azeotropic dehydration. After being cooled to ambient temperature, the reaction mixture was diluted with an aqueous sodium bicarbonate solution and extracted with ethyl acetate three times. The combined organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel (100 g) with dichloromethane as an eluent to afford 2-chloromethyl-1-phenyl-1H-benzimidazole (3.4 g).

後処理

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic layer was washed successively with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residual oil was purified by column chromatography on silica gel (100 g) with dichloromethane as an eluent

出典と根拠

ORDレコード
ord-5720073835484745bf2c062210db3bc8
出典データセット
uspto-grants-1986_01
特許番号
US04563455

関連ノート

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