Water → 1H-Benzimidazole-2-sulfonamide, 6-nitro-N,N,1-triethyl-

HRID 2107028Notes

Reaction equation

HRID 2107028 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([S:14]([NH:17][CH2:18][CH3:19])(=[O:16])=[O:15])[N:11]([CH2:20][CH3:21])[C:10]=2[CH:22]=1)([O-:5])=[O:4].[CH2:23](Br)[CH3:24].O>CN(C)C=O>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([S:14]([N:17]([CH2:23][CH3:24])[CH2:18][CH3:19])(=[O:16])=[O:15])[N:11]([CH2:20][CH3:21])[C:10]=2[CH:22]=1)([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 13985938HCID 13985938, compound

Product 1

HCID 30876041H-Benzimidazole-2-sulfonamide, 6-nitro-N,N,1-triethyl-Yield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

2.6 g (0.11 mol) of sodium hydride are added to a solution of 29.8 g (0.1 mol) of 6-nitro-1,N-diethyl-1H-benzimidazole-2-sulfonamide in 100 ml of dimethylformamide. The solution is stirred for one hour at 40° C., 10.8 g (0.1 mol) of ethyl bromide are added and the mixture is stirred for 12 hours at 50° C. It is poured into water and the product is filtered off and washed with water. The precipitate is recrystallized from ethanol to give 25.6 g (78%) of 6-nitro-1,N,N-triethyl-1H-benzimidazole-2-sulfonamide melting at 90°-1° C.

Workup

  1. stirringthe mixture is stirred for 12 hours at 50° C
  2. filtrationthe product is filtered off
  3. washwashed with water
  4. customThe precipitate is recrystallized from ethanol

Sources & evidence

ORD record
ord-1ceaebf62ec44a91bd78d6722a5de46d
Source dataset
uspto-grants-1990_06
Patent number
US04933338

Reaction notes

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