Chlorosulfonic acid → N-methanesulfonyl-5-chlorosulfonyl-2-aminobenzimidazole

HRID 1166462

반응식

HRID 1166462 반응식
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][S:7]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH2:19])(=[O:9])=[O:8].C(=O)(O)[O-].[Na+]>O>[CH3:6][S:7]([N:10]1[C:14]2[CH:15]=[CH:16][C:17]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:18][C:13]=2[N:12]=[C:11]1[NH2:19])(=[O:8])=[O:9]

참가 물질

5

반응물 3

HCID 24638Chlorosulfonic acidHCID 516892Sodium BicarbonateHCID 229970451-(Methylsulfonyl)-1H-Benzimidazol-2-Amine

생성물 1

HCID 22997216N-methanesulfonyl-5-chlorosulfonyl-2-aminobenzimidazole

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

To 9.5 mL (20 eq., 142 mmol) of well stirred chlorosulfonic acid at ˜25° C. was added N-methanesulfonyl-2-aminobenzimidazole (1.5 g, 7.1 mmol) in small portions over 1C minutes with slight exotherming. The solution was stirred at ˜25° C. for 3.5 hours, then was added dropwise to a well stirred mixture of ice and water. The aqueous solution was slowly basified to pH ˜7.5 with solid sodium bicarbonate and extracted with EtOAc. A precipitate formed in the organic phase which was filtered off and was washed with H20 and dried on the filter to yield 1.23 g of N-methanesulfonyl-5-chlorosulfonyl-2-aminobenzimidazole. HPLC, single peak, ret. time=7.61 min. MS: Obs. M +H@ 310.0 amu.

후처리

  1. additionwas added dropwise to a well
  2. stirringstirred
  3. extractionextracted with EtOAc
  4. customA precipitate formed in the organic phase which
  5. filtrationwas filtered off
  6. washwas washed with H20
  7. customdried on the
  8. filtrationfilter

출처 및 근거

ORD 기록
ord-4e5339decb32429eadc0cf684119054e
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613743B2

연결된 노트

불러오는 중…