Benzaldehyde → HCID 14128199, compound

HRID 1973640Notes

Reaction equation

HRID 1973640 reaction equation
[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[CH:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOCC>[Cl-:9].[CH3:10][N+:11]1[CH:15]=[CH:14][N:13]([CH:1]([O:8][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 13901-MethylimidazoleHCID 7412Benzoyl chloride

Product 1

HCID 14128199HCID 14128199, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ether solution of benzoyl chloride (2.81 g; 0.02 mol) there was added dropwise 1.67 g (0.02 mol) of 1-methylimidazole with stirring. The resulting mixture was evaporated in vacuo and the residue was allowed to react with 2.12 g (0.02 mol) of benzaldehyde at 70° C overnight, using a CaCl2 drying tube to protect it from moisture. After cooling, the reaction mixture was titrated with ether and the solid separated by filtration to give 5.28 g (m.p. 163°-178° ; 80% yield) of crude 1-methyl-3-(α-benzoyloxybenzyl)-imidazolium chloride. After recrystallization from dichloromethane-dioxane, pure 1-methyl-3-(α-benzoyloxybenzyl)-imidazolim chloride was obtained. The mp of the compound was 199°-201° C. The ir and nmr spectra were identical with that of the compound obtained from Method A above.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. temperatureAfter cooling
  3. customthe solid separated by filtration

Sources & evidence

ORD record
ord-df3cf4999060440bb3d46726b4614abd
Source dataset
uspto-grants-1976_12
Patent number
US03998815

Reaction notes

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