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

HRID 1284481

반응식

HRID 1284481 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 202518962-(Chloromethyl)-1-phenyl-1H-benzimidazole수율 36.5%

시약·촉매·용매 2

HCID 241Benzene용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5720073835484745bf2c062210db3bc8
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04563455

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