Water → HCID 18354978, compound

HRID 1533753Notes

Reaction equation

HRID 1533753 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][CH2:22][CH2:23]Br.O>CN(C)C=O>[CH3:1][C:2]1[N:6]([CH2:21][CH2:22][CH3:23])[C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 18355001Methyl 2-methyl-1H-benzimidazole-4-carboxylate

Product 1

HCID 18354978HCID 18354978, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-methyl-1 H-benzimidazole-4-carboxylate (250 mg) in N,N-dimethylformamide (4 ml) were added potassium carbonate (363 mg) and n-propyl bromide at ambient temperature and the mixture was stirred at the same temperature for 2 days. The reaction mixture was poured into water and the aqueous solution was extracted with ethyl acetate. The organic layer was washed with water and brine and the solution was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:1˜1:2˜1:3˜ethyl acetate only) to give methyl 2-methyl-1-propyl-1 H-benzimidazole-4-carboxylate (173 mg) as an oil.

Workup

  1. extractionthe aqueous solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialthe solution was dried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:1˜1:2˜1

Sources & evidence

ORD record
ord-699f0cd223034af3a109e1118af17d2c
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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