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Water → 4-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide

HRID 2239291
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HRID 2239291 반응식
[CH3:1][N:2]([CH3:23])[C:3]([C:5]1[CH:6]=[C:7]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[N:12]=[C:11]([CH3:13])[NH:10][C:9]=2[CH:14]=1)=[O:4].[H-].[Na+].[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.O>CN(C)C=O>[CH3:23][N:2]([CH3:1])[C:3]([C:5]1[CH:6]=[C:7]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[N:12]=[C:11]([CH3:13])[N:10]([S:33]([C:30]3[CH:31]=[CH:32][C:27]([CH3:26])=[CH:28][CH:29]=3)(=[O:35])=[O:34])[C:9]=2[CH:14]=1)=[O:4]
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참가 물질

6

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 68574634N,N,2-Trimethyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxamide

생성물 1

HCID 672201744-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide수율 72%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a suspension of N,N,2-trimethyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxamide (928 mg, 3.0 mmol, STEP 5) in N,N-dimethylformamide (20 mL) was added sodium hydride (60% in mineral oil, 180 mg, 4.50 mmol) at 0° C. After stirring at room temperature for 30 minutes, the reaction mixture was cooled to 0° C. To the mixture was added 4-methylbenzenesulfonyl chloride (572 mg, 3.00 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 2 hours. The mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica gel (gradient elution from dichloromethane only to ethyl acetate only) to afford the title compound as a white solid (1.00 g, 72%).

후처리

  1. temperaturethe reaction mixture was cooled to 0° C
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by column chromatography on silica gel (
  8. washgradient elution from dichloromethane only to ethyl acetate only)

출처 및 근거

ORD 기록
ord-62c4e3b3863c4cf2aba83b2ed36b0ade
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723321B2

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