Butyric Acid → 4-Methyl-2-propyl-1H-benzimidazole

HRID 1636388Notes

Reaction equation

HRID 1636388 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[C:10](O)(=O)[CH2:11][CH2:12][CH3:13].[H-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O>O>[CH3:9][C:3]1[C:2]2[N:1]=[C:10]([CH2:11][CH2:12][CH3:13])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 264Butyric AcidHCID 280Carbon DioxideHCID 10340Sodium CarbonateHCID 175932,3-DiaminotolueneHCID 24758Sodium hydride

Product 1

HCID 219956454-Methyl-2-propyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.00 g (41 mmol) of 2,3-diamino-toluene and 3.7 ml (41 mmol) of butyric acid are stirred in 41 ml of polyphosphoric acid at 120° C. for 3 hours, and the mixture is poured into 410 ml of water and brought to pH=9 with solid sodium hydride. Thereafter, sodium carbonate is added until the evolution of carbon dioxide has ended, the mixture is extracted five times with 100 ml of ethyl acetate each time, the combined organic phases are dried with anhydrous sodium sulphate and the solution is evaportated - finally under a high vacuum; crude weight: 5.89 g.

Workup

  1. extractionthe mixture is extracted five times with 100 ml of ethyl acetate each time
  2. dry with materialthe combined organic phases are dried with anhydrous sodium sulphate

Sources & evidence

ORD record
ord-3c53f231a0d44376b1292d682755468c
Source dataset
uspto-grants-2000_03
Patent number
US06034115

Reaction notes

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