(3-Bromopropyl)benzene → Ethyl 4-methyl-2-(2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl)thiazole-5-carboxylate

HRID 560679Notes

Reaction equation

HRID 560679 reaction equation
C1(CBr)CC1.Br[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:16][C:17]1[N:18]=[C:19]([N:27]2[CH2:31][CH2:30][NH:29][C:28]2=[O:32])[S:20][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[CH3:16][C:17]1[N:18]=[C:19]([N:27]2[CH2:31][CH2:30][N:29]([CH2:7][CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:28]2=[O:32])[S:20][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 81503BromomethylcyclopropaneHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031520Ethyl 4-methyl-2-(2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl)thiazole-5-carboxylateYield 61%

Procedure

Following the procedure as described in Example 10, making variations as required to replace cyclopropylmethyl bromide with 1-bromo-3-phenylpropane to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 61% yield: 1H NMR (300 MHZ, DMSO-d6) δ 7.27-7.13 (m, 5H), 4.27 (q, J=7.2 Hz, 2H), 4.02-3.96 (m, 2H), 3.52-3.46 (m, 2H), 3.37 (t, J=7.2 Hz, 2H), 2.63 (t, J=7.5 Hz, 2H), 2.59 (s, 3H), 1.95-1.88 (m, 2H), 1.23 (t, J=7.2 Hz, 3H): MS (ES+) m/z 374.2 (M+1).

Sources & evidence

ORD record
ord-af0074ead0c647d3824db8baf3635ad0
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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