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

HRID 29148

反応式

HRID 29148 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 10 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 H2O 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 H2O
  7. customdried on the
  8. filtrationfilter

出典と根拠

ORDレコード
ord-91a717dde8e245819f1fa30226f2985e
出典データセット
uspto-grants-2008_09
特許番号
US07419967B2

関連ノート

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