1-(Bromomethyl)-3-(trifluoromethyl)benzene → 1-(5-Acetyl-4-methylthiazol-2-yl)-3-(3-(trifluoromethyl)benzyl)imidazolidin-2-one

HRID 1882398Notes

Reaction equation

HRID 1882398 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]([F:44])([F:43])[C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH2:38]Br>>[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][CH:42]=[C:35]([C:34]([F:33])([F:43])[F:44])[CH:36]=3)[C:27]2=[O:31])=[N:23][C:22]=1[CH3:32])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 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 579198511-(5-Acetyl-4-methylthiazol-2-yl)-3-(3-(trifluoromethyl)benzyl)imidazolidin-2-oneYield 50%

Procedure

Following the procedure as describe 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 3-(trifluoromethyl)benzyl bromide, the title compound was obtained as a yellow solid in 50% yield: mp 149-151° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.70-7.58 (m, 4H), 4.55 (s, 2H), 4.04 (t, J=6.0 Hz, 2H), 3.51 (t, J=6.0 Hz, 2H), 2.51 (s, 3H), 2.45 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 190.9, 160.4, 155.6, 155.1, 138.5, 132.5, 130.4, 129.9 (q, 3JC-F=38 Hz), 126.6, 125.9, 125.1-124.8 (m), 122.9, 47.1, 42.6, 42.4, 30.5, 18.8; MS (ES+) m/z 384.2 (M+1).

Workup

  1. customas describe in Preparation 16

Sources & evidence

ORD record
ord-87c87fa90132457e8b3e59349b9192a1
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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