Hydrochloric Acid → 1-Dimethylaminosulfonyl-2-acetamido-6-hydroxybenzimidazole

HRID 904357Notes

Reaction equation

HRID 904357 reaction equation
[CH3:1][N:2]([CH3:23])[S:3]([N:6]1[C:10]2[CH:11]=[C:12]([O:15]C(=O)C)[CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:19][C:20](=[O:22])[CH3:21])(=[O:5])=[O:4].OO.Cl>CN(C)C=O>[CH3:23][N:2]([CH3:1])[S:3]([N:6]1[C:10]2[CH:11]=[C:12]([OH:15])[CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:19][C:20](=[O:22])[CH3:21])(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 132167171-Dimethylaminosulfonyl-2-acetamido-6-acetoxybenzimidazole

Product 1

HCID 132167161-Dimethylaminosulfonyl-2-acetamido-6-hydroxybenzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Dimethylaminosulfonyl-2-acetamido-6-acetoxybenzimidazole, 170 mg. (0.50 mmole), was dissolved in 3.0 ml. of dimethylformamide and 2.0 ml. of pH 10.0 buffer was added. One-half milliter of three percent hydrogen peroxide was added to the reaction mixture. The reaction mixture was allowed to stir at room temperature for about 10 minutes. The mixture was poured into 50 ml. of 0.1 N hydrochloric acid. The acid mixture was extracted with chloroform. The extract was washed successively with water and saturated sodium chloride solution. The chloroform solution was dried and evaporated in vacuo to yield 102 mg. of 1-dimethylaminosulfonyl-2-acetamido-6-hydroxybenzimidazole, mp. 175°-176° C., after crystallization.

Workup

  1. dissolution(0.50 mmole), was dissolved in 3.0 ml
  2. additionof pH 10.0 buffer was added
  3. additionThe mixture was poured into 50 ml
  4. extractionThe acid mixture was extracted with chloroform
  5. washThe extract was washed successively with water and saturated sodium chloride solution
  6. dry with materialThe chloroform solution was dried
  7. customevaporated in vacuo
  8. customto yield 102 mg
  9. customof 1-dimethylaminosulfonyl-2-acetamido-6-hydroxybenzimidazole, mp. 175°-176° C., after crystallization

Sources & evidence

ORD record
ord-eb10a1af749a4ea1ac18e18a956a3291
Source dataset
uspto-grants-1980_10
Patent number
US04230868

Reaction notes

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