Benzophenone oxime → diphenyl-methanone O-(2-dimethylaminoethyl)-oxime

HRID 450107

Reaction equation

HRID 450107 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:18][CH2:19][N:20]([CH3:22])[CH3:21].[OH-].[K+]>CS(C)=O.O>[CH3:21][N:20]([CH3:22])[CH2:19][CH2:18][O:9][N:8]=[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11324Benzophenone oximeHCID 14797Potassium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 10659548diphenyl-methanone O-(2-dimethylaminoethyl)-oximeYield 26.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of diphenyl-methanone oxime (2 g, 10 mmol) and (2-chloro-ethyl)-dimethyl-amine hydrochloride (1.5 g, 10.4 mmol) in DMSO (20 ml) was added powdered potassium hydroxide (800 mg, 14.3 mmol) and the reaction mixture stirred overnight. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed thoroughly with water and brine, then dried over anhydrous sodium sulphate and filtered. Concentration of the organic layer under reduced pressure gave diphenyl-methanone O-(2-dimethylaminoethyl)-oxime (700 mg, 26%) as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed thoroughly with water and brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-421b1d16853c4246955cf68f76229eb0
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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