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

HRID 1258468
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HRID 1258468 반응식
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:13]=2[CH:12]=[C:11](Br)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:30]1[CH2:34]CCC1.[CH3:35][NH:36][CH3:37]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:13]=2[CH:12]=[C:11]([C:34]([N:36]([CH3:37])[CH3:35])=[O:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

5

반응물 2

HCID 22320367Dimethylamine tetrahydrofuranHCID 67219535HCID 67219535, 화합물

생성물 1

HCID 672201744-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide수율 42%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

A mixture of 4-(benzyloxy)-6-bromo-2-methyl-1-[(4-methylphenyl)sulfonyl]-1H-benzimidazole (53.0 g, 112 mmol, Step 2) and tetrakis(triphenylphosphine)palladium (25.9 g, 22.4 mmol) in 2 mol/L dimethylamine tetrahydrofuran solution (580 mL) was stirred at 65° C. under carbon monoxide gas (1 atm) for 32 hours. The mixture was cooled to room temperature, and diluted with ethyl acetate. The organic mixture was washed with saturated ammonium chloride aqueous solution and brine, dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:2 to 1:3) to afford the title compound as a white solid (21.8 g, 42%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic mixture was washed with saturated ammonium chloride aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:2 to 1:3)

출처 및 근거

ORD 기록
ord-3582d38ded2440489fe358c7274c10ea
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466166B2

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