m-Chloroperbenzoic acid → Dimethylamine

HRID 358427Notes

Reaction equation

HRID 358427 reaction equation
[Cl:1]C1C=CC=C(C(OO)=O)C=1.[CH2:12]([N:15]([CH:30]([CH3:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:29])N(C)C)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:13]=[CH2:14]>C(Cl)(Cl)Cl>[CH3:12][NH:15][CH3:30].[CH2:12]([N:15]([CH:30]([CH3:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([Cl:1])=[O:29])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:13]=[CH2:14]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20447671HCID 20447671, compound

Product 2

HCID 674DimethylamineHCID 20447675HCID 20447675, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.4 g of metachlorperbenzoic acid was added to a chloroform solution of 3.7 g of N-allyl-N-(α-methylbenzyl)-4-(N,N-dimethylcarbamoyl)benzenesulfonamide obtained by reaction between dimethylamine and N-allyl-N-(α-methylbenzyl)-4-chlorocarbonylbenzenesulfonamide. The mixture was reacted under reflux for 2 hours. Thereafter, an aqueous sodium sulfite solution was added to decompose the excess of the peroxide. After washing with an aqueous sodium bicarbonate solution and water, the chloroform solution was dried over anhydrous magnesium sulfate, concentrated and purified by the silica gel chromatography to obtain 3.0 g (77%) of the intended product (Compound No. 163), m.p. 98.0°~100.0° C. The elemental analysis of the product was effected with the results shown below.

Sources & evidence

ORD record
ord-708c6caf31844ca39ca0c9440f9e5a12
Source dataset
uspto-grants-1984_08
Patent number
US04468245

Reaction notes

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