2-Bromobenzyl bromide → 1-(2-Bromobenzyl)-5,5-dimethyl-3-(4-methylsulfanyl-3-trifluoromethylphenyl)imidazolidine-2,4-dione
Reaction equation
[CH3:1][C:2]1([CH3:21])[NH:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[C:3]1=[O:20].[Br:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Br>>[Br:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][N:6]1[C:2]([CH3:21])([CH3:1])[C:3](=[O:20])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[C:5]1=[O:7]Participants
3
Procedure
The reaction of 114.1 with 2-bromobenzyl bromide afforded 1-(2-bromobenzyl)-5,5-dimethyl-3-(4-methylsulfanyl-3-trifluoromethylphenyl)imidazolidine-2,4-dione (115.2). The further reaction with methyl 4-aminobenzoate under conditions as described for the preparation of compound I afforded methyl 4-{2-[5,5-dimethyl-3-(4-methylsulfanyl-3-trifluoromethylphenyl)-2,4-dioxoimidazolidin-1-ylmethyl]phenylamino}benzoate; molecular weight 557.15 (C28H26F3N3O4S); retention time Rt=2.22 min. [B]; MS (ESI): 558.21 (MH+).
Sources & evidence
- ORD record
- ord-feb20617b89c46ad910a3fab0665cc69
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759366B2
Reaction notes
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