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

HRID 328748Notes

Reaction equation

HRID 328748 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-31a5cfe792704bff8d741d9297b08f35
Source dataset
uspto-grants-1977_04
Patent number
US04018790

Reaction notes

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