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

HRID 1447178Notes

Reaction equation

HRID 1447178 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-cc3da3ae9030418baaff05d387908f66
Source dataset
uspto-grants-1982_02
Patent number
US04316021

Reaction notes

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