Ammonia → 3-(1-Methyl-1H-benzimidazol-2-yl)propan-1-ol

HRID 2292137Notes

Reaction equation

HRID 2292137 reaction equation
Cl.Cl.[CH3:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11].[C:12]1(=O)[O:16][CH2:15][CH2:14][CH2:13]1.N>Cl>[CH3:3][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:11]=[C:12]1[CH2:13][CH2:14][CH2:15][OH:16]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 7302Gamma-ButyrolactoneHCID 91296N-Methyl-o-phenylenediamine dihydrochloride

Product 1

HCID 45852153-(1-Methyl-1H-benzimidazol-2-yl)propan-1-olYield 71.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-Methyl-ortho-phenylenediamine dihydrochloride (4.88 g), and butyrolactone (3.22 g) were stirred at reflux for 18 hours in 4N hydrochloric acid (25 ml). The reaction mixture was cooled, the pH adjusted to 8 with concentrated aqueous ammonia and filtered. The solid was recrystallised from ethyl acetate to yield the title compound as a white solid (3.39 g 71%), m.p. 107° C. Found: C, 69.22; H, 7.38; N, 14.73. C11H14N2O requires C, 69.45; H, 7.42; N, 14.72%.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customThe solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-84859d92112b492592888741df5973db
Source dataset
uspto-grants-1989_01
Patent number
US04801598

Reaction notes

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