4-Fluorobenzyl bromide → 1-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-fluorobenzyl)imidazolidin-2-one

HRID 1882397Notes

Reaction equation

HRID 1882397 reaction equation
CC1N=C(N2C(=O)NN=C2)SC=1C(OCC)=O.[C:18]([C:21]1[S:25][C:24]([N:26]2[CH2:30][CH2:29][NH:28][C:27]2=[O:31])=[N:23][C:22]=1[CH3:32])(=[O:20])[CH3:19].[F:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1>>[C:18]([C:21]1[S:25][C:24]([N:26]2[CH2:30][CH2:29][N:28]([CH2:38][C:37]3[CH:40]=[CH:41][C:34]([F:33])=[CH:35][CH:36]=3)[C:27]2=[O:31])=[N:23][C:22]=1[CH3:32])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 579197381-(5-Acetyl-4-methylthiazol-2-yl)imidazolidin-2-oneHCID 57920013ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

Product 1

HCID 579197651-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-fluorobenzyl)imidazolidin-2-oneYield 98%

Procedure

Following the procedure as described in Preparation 16, making variations as required to replace ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate with 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one to react with 4-fluorobenzyl bromide, the title compound was obtained as a yellow solid in 98% yield: 1H NMR (300 MHz, CDCl3) δ 7.32-7.22 (m, 2H), 7.07-6.97 (m, 2H), 4.45 (s, 2H), 4.10-4.04 (m, 2H), 3.48-3.37 (m, 2H), 2.67 (s, 3H), 2.38 (s, 3H); MS (ES+) m/z 334.1 (M+1).

Workup

  1. customas described in Preparation 16

Sources & evidence

ORD record
ord-556be5cf95aa4a70b0a50a4ceb65c126
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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