2-Bromobenzyl bromide → 4-[3-(2-Bromo-4-methoxybenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile
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:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[CH2:40]Br>>[Br:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[CH2:40][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
Product 1
Procedure
Compound 110.2 was prepared as described for example 1.2, by reacting compound 1.1, instead of with 2-bromobenzyl bromide, with 2-bromo-1-bromomethyl-4-methoxybenzene (prepared by N-bromosuccinimide bromination from 2-bromo-4-methoxy-1-methylbenzene; 1H NMR: 7.56, d, 1H, 7.23, s, 1H, 7.0, d, 1H, 4.74, s, 2H; 3.8, s, 3H). 4-[3-(2-Bromo-4-methoxybenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile was obtained. (Molecular weight 495.04 (C21H17BrF3N3O3); 1H NMR: 8.38, d, 1H, 8.25, s, 1H, 8.1, d, 1H, 7.5, d, 1H, 7.22, s, 1H, 6.95, d, 1H, 4.6, s, 2H, 3.79, s, 3H, 1.4, s, 6H.
Sources & evidence
- ORD record
- ord-cc9225f1ab834b1c9c08a2b6afab3f26
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759366B2
Reaction notes
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