4-Bromo-1,1,1-trifluorobutane → 1-(5-Acetyl-4-methylthiazol-2-yl)-3-(4,4,4-trifluorobutyl)imidazolidin-2-one

HRID 554923Notes

Reaction equation

HRID 554923 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].Br[CH2:34][CH2:35][CH2:36][C:37]([F:40])([F:39])[F:38]>>[C:18]([C:21]1[S:25][C:24]([N:26]2[CH2:30][CH2:29][N:28]([CH2:34][CH2:35][CH2:36][C:37]([F:40])([F:39])[F:38])[C:27]2=[O:31])=[N:23][C:22]=1[CH3:32])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 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 579197941-(5-Acetyl-4-methylthiazol-2-yl)-3-(4,4,4-trifluorobutyl)imidazolidin-2-oneYield 60%

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 4-bromo-1,1,1-trifluorobutane instead of bromomethyl-2,2-difluorocyclopropane, the title compound was obtained as a yellow solid in 60% yield: mp 108-110° C.; 1H NMR (300 MHz, DMSO-d6) δ 3.97 (t, J=9.0 Hz, 2H), 3.57-3.47 (m, 2H), 3.28 (t, J=9.0 Hz, 2H), 2.50 (s, 3H), 2.40 (s, 3H), 2.32-2.19 (m, 2H), 1.76-1.62 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 155.9, 155.8, MS (ES+) m/z 336.9 (M+1).

Workup

  1. customas describe in Preparation 16

Sources & evidence

ORD record
ord-add9b24f4de64786848f2cec8824950e
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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