Dimethyl Sulfoxide → 1-Isopropylsulfonyl-2-amino-6-(alpha-hydroxy-alpha-methylsulfinylmethylbenzyl)benzimidazole

HRID 904831노트

반응식

HRID 904831 반응식
C([Li])CCC.[CH3:6][S:7]([CH3:9])=[O:8].[CH:10]([S:13]([N:16]1[C:20]2[CH:21]=[C:22]([C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[NH2:33])(=[O:15])=[O:14])([CH3:12])[CH3:11]>O1CCCC1>[CH:10]([S:13]([N:16]1[C:20]2[CH:21]=[C:22]([C:25]([OH:32])([CH2:6][S:7]([CH3:9])=[O:8])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[NH2:33])(=[O:14])=[O:15])([CH3:12])[CH3:11]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 30173892-Amino-6-benzoyl-1-((isopropyl)sulphonyl)-1H-benzimidazoleHCID 178418339Butyllithium

생성물 1

HCID 204777381-Isopropylsulfonyl-2-amino-6-(alpha-hydroxy-alpha-methylsulfinylmethylbenzyl)benzimidazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

Lithium methyl sulfinyl carbanion was prepared by reacting 37 ml. of a 1.6 M solution of n-butyl lithium in tetrahydrofuran with 5 ml. of dimethyl sulfoxide dissolved in 70 ml. of tetrahydrofuran. After stirring the reaction mixture under nitrogen for thirty minutes at 0°-5° C., a mixture of 4.0 g. of 1-isopropylsulfonyl-2-amino-6-benzoylbenzimidazole in 60 ml. of tetrahydrofuran was added in one portion. The reaction mixture was stirred for one hour at 0° C., and then was warmed to room temperature and stirred for an additional twelve hours at 24° C., followed by thirty-six hours of stirring at 50° C. The reaction mixture next was diluted with 100 ml. of water, and the organic solvent was removed by evaporation under reduced pressure. The aqueous mixture was acidified to pH 2 with 1 N hydrochloric acid, and then filtered. The filtrate was neutralized with sodium carbonate, and the product was extracted therefrom into ethyl acetate. The extracts were combined and the solvent was removed by evaporation under reduced pressure to provide 1-isopropylsulfonyl-2-amino-6-(α-hydroxy-α-methylsulfinylmethylbenzyl)benzimidazole.

후처리

  1. additiona mixture of 4.0 g
  2. stirringThe reaction mixture was stirred for one hour at 0° C.
  3. stirringstirred for an additional twelve hours at 24° C.
  4. waitfollowed by thirty-six hours
  5. stirringof stirring at 50° C
  6. additionThe reaction mixture next was diluted with 100 ml
  7. customof water, and the organic solvent was removed by evaporation under reduced pressure
  8. filtrationfiltered
  9. extractionthe product was extracted
  10. customthe solvent was removed by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-bc44c56c477c4cc88d4f7a425a72f77c
출처 데이터셋
uspto-grants-1983_12
특허 번호
US04420479

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