Benzoyl Peroxide → N-[2-(bromoacetyl)phenyl]methanesulfonamide

HRID 466355Notes

Reaction equation

HRID 466355 reaction equation
[Br:1][CH2:2][C:3](C1C=CC(NS(C2C=CC(C)=CC=2)(=O)=O)=CC=1)=[O:4].C([C:25]1[CH:41]=[CH:40][C:28]([NH:29][S:30]([C:33]2C=CC(C)=CC=2)(=[O:32])=[O:31])=[CH:27][CH:26]=1)(=O)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CCOCC>[Br:1][CH2:2][C:3]([C:27]1[CH:26]=[CH:25][CH:41]=[CH:40][C:28]=1[NH:29][S:30]([CH3:33])(=[O:31])=[O:32])=[O:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 563797N-(4-acetylphenyl)-4-methylbenzene-1-sulfonamideHCID 16637184N-[4-(2-Bromoacetyl)phenyl]-4-methylbenzenesulfonamide

Product 1

HCID 18380501N-[2-(bromoacetyl)phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a similar manner 4'-(2-bromoacetyl)-p-toluenesulfonanilide, (m.p. 174°-1765° with decomposition,) can be prepared by bromination of 4'-acetyl-p-toluenesulfonanilide (Preparation 1) [See R. H. Vloth, et al., J. Med. Chem. 9, 88 (1966)]. For this preparation anhydrous ether can also be used as solvent; benzoyl peroxide can be used as a catalyst. The product is crystallized from acetonitrile.

Workup

  1. customThe product is crystallized from acetonitrile

Sources & evidence

ORD record
ord-ff169a4c8b5940bf8693f970e8c7b5ac
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

Loading…