Calcium Carbonate → 6-bromo-1,3-dihydro-1-(2-dimethylaminoethyl)-5-methoxy-2H-benzimidazol-2-one

HRID 373062노트

반응식

HRID 373062 반응식
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=2[NH:7][C:6]1=[O:16].C(=O)([O-])[O-].[Ca+2].[Br-:23].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>CO.ClCCl>[Br:23][C:11]1[C:12]([O:14][CH3:15])=[CH:13][C:8]2[NH:7][C:6](=[O:16])[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:17])[C:9]=2[CH:10]=1

참가 물질

6

반응물 3

HCID 10112Calcium CarbonateHCID 198113461,3-dihydro-1-(2-dimethylaminoethyl)-5-methoxy-2H-benzimidazol-2-oneHCID 53442637Benzyltrimethylammoniumtribromide

생성물 1

HCID 198113066-bromo-1,3-dihydro-1-(2-dimethylaminoethyl)-5-methoxy-2H-benzimidazol-2-one수율 157%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1,3-dihydro-1-(2-dimethylaminoethyl)-5-methoxy-2H-benzimidazol-2-one (0.28 g) in methanol (10 ml) and dichloromethane (15 ml) were added calcium carbonate (0.25 g) and benzyltrimethylammonium tribromide (0.49 g). The reaction mixture was stirred at room temperature for 16 hours and the insoluble matter was filtered off. The solvent was then distilled off under reduced pressure and the residue was diluted with 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: chloroform:methanol=10:1) to give 0.35 g of 6-bromo-1,3-dihydro-1-(2-dimethylaminoethyl)-5-methoxy-2H-benzimidazol-2-one.

후처리

  1. filtrationthe insoluble matter was filtered off
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionthe residue was diluted with 1N aqueous sodium hydroxide solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (eluent: chloroform:methanol=10:1)

출처 및 근거

ORD 기록
ord-ec3d0d825e084b20aff600a913f88785
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162318

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