Hydrochloric Acid → 2-(Hydroxymethyl)-1H-benzimidazole

HRID 2071589Notes

Reaction equation

HRID 2071589 reaction equation
Cl.[C:2]1([NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[C:10](O)(=O)[CH2:11][OH:12]>>[OH:12][CH2:11][C:10]1[NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 757Glycolic AcidHCID 7243O-Phenylenediamine

Product 1

HCID 785692-(Hydroxymethyl)-1H-benzimidazole

Procedure

To 150 ml. of 4N hydrochloric acid were added 10.8 gms. (100 mmoles.) of o-phenylenediamine and 11.4 gms. (150 mmoles.) of glycolic acid. The mixture was refluxed for 40 minutes. The solution then was cooled, filtered, and neutralized by the addition of concentrated ammonium hydroxide. The title compound precipitated and was filtered and dried to obtain 4 gms. of product.

Workup

  1. temperatureThe mixture was refluxed for 40 minutes
  2. temperatureThe solution then was cooled
  3. filtrationfiltered
  4. additionneutralized by the addition of concentrated ammonium hydroxide
  5. customThe title compound precipitated
  6. filtrationwas filtered
  7. customdried
  8. customto obtain 4 gms

Sources & evidence

ORD record
ord-60b1b0d8b2f44b04afd643828fab3c7e
Source dataset
uspto-grants-1977_09
Patent number
US04048161

Reaction notes

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