2-Bromobenzyl bromide → 3-Bromo-4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-ylmethyl]-N,N-dimethylbenzenesulfonamide

HRID 2356650Notes

Reaction equation

HRID 2356650 reaction equation
[CH3:1][C:2]1([CH3:21])[C:6](=[O:7])[N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[C:4](=[O:20])[NH:3]1.BrC1C=CC=CC=1CBr.[Br:31][C:32]1[CH:33]=[C:34]([S:40]([N:43]([CH3:45])[CH3:44])(=[O:42])=[O:41])[CH:35]=[CH:36][C:37]=1[CH2:38]Br>>[Br:31][C:32]1[CH:33]=[C:34]([S:40]([N:43]([CH3:44])[CH3:45])(=[O:41])=[O:42])[CH:35]=[CH:36][C:37]=1[CH2:38][N:3]1[C:2]([CH3:21])([CH3:1])[C:6](=[O:7])[N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:17])[F:18])[CH:9]=2)[C:4]1=[O:20]

Participants

4

Reactant 3

HCID 769652-Bromobenzyl bromideHCID 111622854-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrileHCID 686781563-bromo-4-bromomethyl-N,N-dimethylbenzenesulfonamide

Product 1

HCID 686771073-Bromo-4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-ylmethyl]-N,N-dimethylbenzenesulfonamide

Procedure

Compound 146.2 was prepared as described for example 1.2, by reacting compound 1.1, instead of with 2-bromobenzyl bromide, with 3-bromo-4-bromomethyl-N,N-dimethylbenzenesulfonamide (146.3, prepared by reacting 3-bromo-4,N,N-trimethylbenzenesulfonamide with N-bromosuccinimide and N,N′-azobis(2-methylpropionitrile) in tetrachloromethane). 3-Bromo-4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-ylmethyl]-N,N-dimethylbenzenesulfonamide was obtained. (Molecular weight 572.03 (C22H20BrF3N4O4S); retention time Rt=2.38 min. [B]; MS (ESI): 573.25 (MH+).

Sources & evidence

ORD record
ord-b48e30df14314521a80ac652292aa868
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

Loading…