Dimethylformamide → 5-(5-isoquinolylsulfanyl)-6-nitro-2,3-dihydro-1H-benzo[d]imidazol-2-one

HRID 619737

반응식

HRID 619737 반응식
CN(C=O)C.F[C:7]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:10]2[NH:11][C:12](=[O:14])[NH:13][C:9]=2[CH:8]=1.[CH:20]1[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([SH:30])[C:24]=2[CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH:20]1[C:29]2[C:24](=[C:25]([S:30][C:7]3[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:10]4[NH:11][C:12](=[O:14])[NH:13][C:9]=4[CH:8]=3)[CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][N:21]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 110519635-IsoquinolinethiolHCID 218470085-Fluoro-6-nitrobenzoimidazolinone

생성물 1

HCID 218469475-(5-isoquinolylsulfanyl)-6-nitro-2,3-dihydro-1H-benzo[d]imidazol-2-one수율 40.9%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To a DMF solution 15 ml of 5-fluoro-6-nitrobenzoimidazolinone 500 mg (2.5 mmol) and 5-isoquinolinethiol 450 mg (2.8 mmol), potassium carbonate 550 mg (4.0 mmol) was added, and the mixture was heated with stirring for 2 hours at 100° C. After adding water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated water solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from methanol, and 5-(5-isoquinolylsulfanyl)-6-nitro-2,3-dihydro-1H-benzo[d]imidazol-2-one 346 mg (40.3%) was obtained.

후처리

  1. temperaturethe mixture was heated
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated water solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from methanol

출처 및 근거

ORD 기록
ord-b766ee850f0e49c0b6bbf859dc296e8f
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05959107

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