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

HRID 1166462

反応式

HRID 1166462 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4e5339decb32429eadc0cf684119054e
出典データセット
uspto-grants-2003_09
特許番号
US06613743B2

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