Benzyl Bromide → Ethyl 4-methyl-2-(2-oxo-3-phenethylimidazolidin-1-yl)thiazole-5-carboxylate

HRID 560577Notes

Reaction equation

C(Br)C1C=CC=CC=1.I[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:18][C:19]1[N:20]=[C:21]([N:29]2[CH2:33][CH2:32][NH:31][C:30]2=[O:34])[S:22][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]>>[CH3:18][C:19]1[N:20]=[C:21]([N:29]2[CH2:33][CH2:32][N:31]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:30]2=[O:34])[S:22][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 28503Benzene, (2-iodoethyl)-

HCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031553Ethyl 4-methyl-2-(2-oxo-3-phenethylimidazolidin-1-yl)thiazole-5-carboxylateYield 35%

Procedure

Following the procedure as described in Example 5, making variations to replace benzyl bromide with (2-iodoethyl)benzene to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 35% yield: 1H NMR (300 MHz, CDCl3) δ 7.31-7.20 (m, 5H), 4.25 (q, 1=7.2 Hz, 2H), 4.02 (t, J=7.8 Hz, 2H), 3.57 (t, J=7.2 Hz, 2H), 3.42 (t, J=7.8 Hz, 2H), 2.89 (t, J=7.2 Hz, 2H), 2.59 (s, 3H), 1.31 (t, J=7.2 Hz, 3H): MS (ES+) m/z 360.2 (M+1).

Sources & evidence

ORD record: ord-b2b82294777643fa8a42673247d55c15
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

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