4-Fluorobenzyl bromide → Ethyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 2067478Notes

Reaction equation

HRID 2067478 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.[CH3:22][C:23]1[N:24]=[C:25]([N:33]2[CH2:37][CH2:36][NH:35][C:34]2=[O:38])[S:26][C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:35]2[CH2:36][CH2:37][N:33]([C:25]3[S:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:23]([CH3:22])[N:24]=3)[C:34]2=[O:38])=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 57919911Ethyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 69%

Procedure

Following the procedure as described in Example 13, making variations as required to replace 4-(trifluoromethyl)benzyl bromide with 1-(bromomethyl)-4-fluorobenzene to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained as a colorless solid in 69% yield: 1H NMR (300 MHz, CDCl3) δ 7.31-7.28 (m, 2H), 7.07-7.02 (m, 2H), 4.47 (s, 2H), 4.29 (q, J=6.0 Hz, 2H), 4.08 (t, J=9.0 Hz, 2H), 3.46 (t, J=9.0 Hz, 2H), 2.62 (s, 3H), 1.34 (t, J=6.0 Hz, 3H); MS (ES+) m/z 364.1.0 (M+1).

Sources & evidence

ORD record
ord-a713e9553bdd4bf181393501f8e77be6
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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