Butyl bromide → 1-butyl-2-methylbenzimidazole

HRID 1638765Notes

Reaction equation

HRID 1638765 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:12]([N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[CH3:1])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 119842-MethylbenzimidazoleHCID 14798Sodium Hydroxide

Product 1

HCID 3354721-butyl-2-methylbenzimidazoleYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-methylbenzimidazole (1.32 g, 0.01 mol), 1-bromobutane (1.21 g, 0.01 mol), 50% aqueous sodium hydroxide (5 ml), toluene (20 ml) and 0.5 mmol of compound 1 was stirred at 80°-85° C. for 3 hours. After that time, the resulting mixture was allowed to cool to room temperature and the organic layer was separated, extracted with concentrated hydrochloric acid (3×20 ml). The acidic solution was neutralized with 20% sodium hydroxide, extracted with toluene (3×15 ml), dried over magnesium sulphate and evaporated to give a residue which was distilled at reduced pressure (0.4-0.5 mm 162°-6° C.) to give 1-n-butyl-2-methylbenzimidazole. Yield: 65%.

Workup

  1. customthe organic layer was separated
  2. extractionextracted with concentrated hydrochloric acid (3×20 ml)
  3. extractionextracted with toluene (3×15 ml)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto give a residue which
  7. distillationwas distilled at reduced pressure (0.4-0.5 mm 162°-6° C.)

Sources & evidence

ORD record
ord-de415b23739148b48d51e953413e97d5
Source dataset
uspto-grants-1989_11
Patent number
US04880894

Reaction notes

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