Water → HCID 13295290, compound

HRID 1253135Notes

Reaction equation

HRID 1253135 reaction equation
[N:1]1([CH2:6][C:7](=[O:16])[C:8]([CH:11]2[O:15][CH2:14][CH2:13][O:12]2)([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[K+].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.O>CS(C)=O>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][CH:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:7](=[O:16])[C:8]([CH:11]2[O:15][CH2:14][CH2:13][O:12]2)([CH3:10])[CH3:9])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14797Potassium HydroxideHCID 132952943-(1,3-Dioxolan-2-yl)-1-(1H-imidazol-1-yl)-3-methylbutan-2-one

Product 1

HCID 13295290HCID 13295290, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

30 g (0.131 mol) of 1-(imidazol-1-yl)-3-(dioxolan-2-yl)-3-methyl-butan-2-one are dissolved in 130 ml of dimethylsulphoxide, 7.5 g of powdered potassium hydroxide are added at 10° C., and 21 g of 4-chlorobenzyl chloride (0.131 mol), dissolved in 30 ml of dimethylsulphoxide, are added dropwise. After stirring has been carried out for 15 hours at 20° C., the suspension is poured onto 500 ml of water, the mixture is extracted with 600 ml of methylene chloride, the organic phase is extracted with 1 liter of water in each case, and the solvent is distilled off. The oily residue is taken up in 300 ml of diethyl ether, the other phase is filtered and the solvent is distilled off. 14 g (30.6% of theory) of 1-(4-chlorophenyl)-4-(dioxolan-2-yl)-2-(imidazol-1-yl)-4-methyl-pentan-3-one of refractive index nD20 =1.5490 are obtained.

Workup

  1. additionare added dropwise
  2. extractionthe mixture is extracted with 600 ml of methylene chloride
  3. extractionthe organic phase is extracted with 1 liter of water in each case
  4. distillationthe solvent is distilled off
  5. filtrationthe other phase is filtered
  6. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-5cee62733f4c4cc0a770e065e1800278
Source dataset
uspto-grants-1988_05
Patent number
US04747869

Reaction notes

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