Hydrochloride methanol → 1-(3-Amino-3-methyl-butyl)-1,3-dihydro-benzimidazol-2-one

HRID 1095401Notes

Reaction equation

HRID 1095401 reaction equation
[CH3:1][C:2]([NH:16]C=O)([CH3:15])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].Cl.CO>>[NH2:16][C:2]([CH3:15])([CH3:1])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14]

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 60209130HCID 60209130, compound

Product 1

HCID 131744871-(3-Amino-3-methyl-butyl)-1,3-dihydro-benzimidazol-2-one

Procedure

A mixture of N-[1,1-dimethyl-3-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)propyl]formamide (1.1 g) and hydrogen chloride-methanol (80-90% methanol, 18 mL) was stirred at rt for 50 h. The mixture was concentrated in vacuo and the residue was basified by aq. potassium carbonate and the mixture was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to give 0.81 g (3.7 mmol, 73% for 3 steps) of the title compound.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c1ca561ee14c4682a0fb1bc14272255a
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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