m-Chloroperbenzoic acid → HCID 12188112, compound

HRID 613188Notes

Reaction equation

HRID 613188 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>C(Cl)Cl>[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N+:19][O-:6])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 709674-(Dimethylamino)benzonitrile

Product 1

HCID 12188112HCID 12188112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 13.8 g of meta-chloroperoxybenzoic acid in 200 ml of methylene chloride was added dropwise to a solution of 11.7 g of para-dimethylaminobenzonitrile in 80 ml of methylene chloride at a temperature of from 0° C. to -5° C. over the course of two hours. When no more peroxide was detectable (negative KI test), the solvent was evaporated on a rotary evaporator. This gave 25.7 g of the meta-chlorobenzoic acid salt of para-dimethylaminobenzonitrile N-oxide. Pure para-dimethylaminobenzonitrile N-oxide was isolated by chromatography on aluminum oxide.

Workup

  1. customthe solvent was evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-519f5ffc22684ac3a9fc395c2d9ce093
Source dataset
uspto-grants-1999_12
Patent number
US06007583

Reaction notes

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