Cyanogen Bromide → 6-(Methanesulfonyl)-1H-benzimidazol-2-amine

HRID 1111773Notes

Reaction equation

HRID 1111773 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH2:12])[CH:6]=1)(=[O:4])=[O:3].[N:13]#[C:14]Br>O>[NH2:13][C:14]1[NH:12][C:7]2[CH:6]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:10]=[CH:9][C:8]=2[N:11]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 69514184-(methylsulfonyl)benzene-1,2-diamine

Product 1

HCID 128379916-(Methanesulfonyl)-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One mole, 186.1 g., of 4-methylsulfonyl-o-phenylenediamine was suspended in 1.2 l. of water with stirring. One mole, 106 g., of cyanogenbromide was added portionwise to the reaction mixture. The reaction mixture was stirred for 4 hours and then filtered. Sodium hydroxide, 39 g. (1 m.) in 500 ml. of water, was added to the filtrate. The aqueous mixture was cooled in an ice bath and the product crystallized. The product was collected and dried before crystallization from ethanol-ether; yield 200 g., m.p. 233°-238° C.

Workup

  1. filtrationfiltered
  2. additionof water, was added to the filtrate
  3. temperatureThe aqueous mixture was cooled in an ice bath
  4. customthe product crystallized
  5. customThe product was collected
  6. dry with materialdried before crystallization from ethanol-ether

Sources & evidence

ORD record
ord-01280097e53f4ab884f9ec05f9d9ee2b
Source dataset
uspto-grants-1978_10
Patent number
US04118573

Reaction notes

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