Glycolic Acid → 5-Chloro-2-(hydroxymethyl)-1H-benzimidazole-6-sulfonamide

HRID 904846Notes

Reaction equation

HRID 904846 reaction equation
[NH2:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([S:10](=[O:13])(=[O:12])[NH2:11])=[CH:5][C:3]=1[NH2:4].[C:14](O)(=O)[CH2:15][OH:16]>Cl>[Cl:9][C:7]1[C:6]([S:10](=[O:12])(=[O:13])[NH2:11])=[CH:5][C:3]2[NH:4][C:14]([CH2:15][OH:16])=[N:1][C:2]=2[CH:8]=1

Participants

4

Reactant 2

HCID 757Glycolic AcidHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132897035-Chloro-2-(hydroxymethyl)-1H-benzimidazole-6-sulfonamideYield 23.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 11.0 g of 2-amino-4-chloro-5-sulfamylaniline in 50 ml of 4 N hydrochloric acid was added 5.6 g of glycolic acid. After refluxing for 6 hours, the resulting solid was collected by filtration and then added with stirring to 200 ml of 38% ammonium hydroxide; the pink precipitate was then collected and suspended in water with stirring at 60° for 20 minutes. Recrystallization of the solid from methanol provided 3.0 g of colorless crystals, m.p. 247°-250°.

Workup

  1. temperatureAfter refluxing for 6 hours
  2. filtrationthe resulting solid was collected by filtration
  3. additionadded
  4. customthe pink precipitate was then collected
  5. stirringwith stirring at 60° for 20 minutes
  6. customRecrystallization of the solid from methanol

Sources & evidence

ORD record
ord-02a29ee8c123433f858e32ce854e779f
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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