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

HRID 1166462

Reaction equation

HRID 1166462 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4e5339decb32429eadc0cf684119054e
Source dataset
uspto-grants-2003_09
Patent number
US06613743B2

Linked notes

Loading…