Ammonia → 4-benzyloxy-2-(1-hydroxyethyl)-1-methyl-1H-benzimidazole

HRID 2287575Notes

Reaction equation

HRID 2287575 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH2:17])=[C:11]([CH:14]=[CH:15][CH:16]=1)[NH:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](O)(=O)[CH:19]([CH3:21])[OH:20].Cl.N>>[CH2:1]([O:8][C:9]1[C:10]2[N:17]=[C:18]([CH:19]([OH:20])[CH3:21])[N:12]([CH3:13])[C:11]=2[CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 612Lactic AcidHCID 104895412-amino-3-benzyloxy-N-methylaniline

Product 1

HCID 106605464-benzyloxy-2-(1-hydroxyethyl)-1-methyl-1H-benzimidazoleYield 19.4%

Procedure

A mixture of 3-benzyloxy-2-amino-N-methylaniline (400 mg), lactic acid (473.8 mg) and 4N hydrochloric acid (1.6 ml) was refluxed for 1.5 hours. After cooling, the mixture was adjusted to pH 8 with 28% ammonia solution, and extracted with ethyl acetate. The 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 (ethyl acetate:n-hexane=2:1, v/v) to give 4-benzyloxy-2-(1-hydroxyethyl)-1-methyl-1H-benzimidazole (96.2 mg).

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe 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 (ethyl acetate

Sources & evidence

ORD record
ord-5b714ab15f514366a205627f277004f7
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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