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

HRID 1882402Notes

Reaction equation

HRID 1882402 reaction equation
C1(CBr)CC1.[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=1.[C:15]([C:18]1[S:22][C:21]([N:23]2[CH2:27][CH2:26][NH:25][C:24]2=[O:28])=[N:20][C:19]=1[CH3:29])(=[O:17])[CH3:16]>>[C:15]([C:18]1[S:22][C:21]([N:23]2[CH2:27][CH2:26][N:25]([CH2:11][C:10]3[CH:13]=[CH:14][C:7]([F:6])=[CH:8][CH:9]=3)[C:24]2=[O:28])=[N:20][C:19]=1[CH3:29])(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 81503BromomethylcyclopropaneHCID 579197381-(5-Acetyl-4-methylthiazol-2-yl)imidazolidin-2-one

Product 1

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

Procedure

Following the procedure as describe in Preparation 19, making variations as required to replace cyclopropylmethyl bromide with 4-fluorobenzyl bromide to react with 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one, the title compound was obtained in 98% yield (3.27 g): 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 describe in Preparation 19

Sources & evidence

ORD record
ord-2e22eb6fa0194d49a9a6639f1c61cfda
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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