Methyl iodide → HCID 21273510, compound

HRID 1382931Notes

Reaction equation

HRID 1382931 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][C:16]1[NH:17][C:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:35]I>CN(C)C=O>[CH2:1]([O:8][C:9]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][C:16]1[N:20]([CH3:35])[C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:18]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21273475HCID 21273475, compound

Product 1

HCID 21273510HCID 21273510, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 6.4 g (0.015 mol) of 2-[3-(N-benzyloxycarbonylmethylamino)propyl]-4,5-diphenylimidazole in 120 ml of dimethylformamide is treated at 15°-20° under argon with 0.018 mol of sodium hydride (0.8 g of a 55% dispersion in mineral oil) and thereupon stirred at room temperature for a further 30 minutes. A solution of 1.85 ml (0.03 mol) of methyl iodide in 10 ml of dimethylformamide is added thereto at 15°-20° within 15 minutes and the mixture is stirred at room temperature for a further 3 hours. After concentration under reduced pressure the residue is partitioned between ice-water and ethyl acetate. The organic phase, dried over sodium sulphate, is evaporated and the residual oil is chromatographed on 100 g of silica gel with ethyl acetate as the elution agent. The 2-[3-(N-benzyloxycarbonylmethylamino)propyl]-1-methyl-4,5-diphenylimidazole (6.4 g of oil) obtained is dissolved in 300 ml of methanol and hydrogenated at room temperature and normal pressure in the presence of 1 g of 5% palladium-on-active charcoal. The product, isolated in the usual manner, is chromatographed on 70 g of silica gel with methanol/concentrated ammonium hydroxide (100:1) as the elution agent. There are obtained 2.95 g (64%) of 1-methyl-2-[3-(methylamino)propyl]-4.5-diphenylimidazole as a thick oil.

Workup

  1. waitat 15°-20° within 15 minutes
  2. stirringthe mixture is stirred at room temperature for a further 3 hours
  3. concentrationAfter concentration under reduced pressure the residue
  4. customis partitioned between ice-water and ethyl acetate
  5. dry with materialThe organic phase, dried over sodium sulphate
  6. customis evaporated
  7. customthe residual oil is chromatographed on 100 g of silica gel with ethyl acetate as the elution agent

Sources & evidence

ORD record
ord-e9976927553449408da5aa4efcbf4fee
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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