Hydrochloric Acid → 2-isopropyl-1-methyl-1H-benzo[d]imidazol-4-ol

HRID 2287579Notes

Reaction equation

HRID 2287579 reaction equation
C([O:8][C:9]1[C:10]([NH2:17])=[C:11]([CH:14]=[CH:15][CH:16]=1)[NH:12][CH3:13])C1C=CC=CC=1.[C:18](O)(=O)[CH:19]([CH3:21])[CH3:20].Cl>>[OH:8][C:9]1[C:10]2[N:17]=[C:18]([CH:19]([CH3:21])[CH3:20])[N:12]([CH3:13])[C:11]=2[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6590Isobutyric AcidHCID 104895412-amino-3-benzyloxy-N-methylaniline

Product 1

HCID 212547552-isopropyl-1-methyl-1H-benzo[d]imidazol-4-olYield 6.6%

Procedure

A mixture of 3-benzyloxy-2-amino-N-methylaniline (600 mg), isobutyric acid (243 mg) and 4N hydrochloric acid (3.5 ml) was refluxed for 3 hours, and the solvent was removed in vacuo. Chloroform and saturated sodium bicarbonate solution were added to the residue. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1, v/v) to give 4-hydroxy-2-isopropyl-1-methyl-1H-benzimidazole (33 mg).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customthe solvent was removed in vacuo
  3. additionChloroform and saturated sodium bicarbonate solution were added to the residue
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-f20572a00b3b4d87abf9944e2e9af23b
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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