Benzyl Bromide → Ethyl 2-(3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)acetate

HRID 560590Notes

Reaction equation

C(Br)C1C=CC=CC=1.Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH2:16]([NH:23][C:24]([C:26]1[S:30][C:29]([N:31]2[CH2:35][CH2:34][NH:33][C:32]2=[O:36])=[N:28][C:27]=1[CH3:37])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([NH:23][C:24]([C:26]1[S:30][C:29]([N:31]2[CH2:35][CH2:34][N:33]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:32]2=[O:36])=[N:28][C:27]=1[CH3:37])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 7748Ethyl bromoacetate

HCID 59481185N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 59481247Ethyl 2-(3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)acetateYield 38%

Procedure

Following the procedure as described in Example 5, making variations to replace benzyl bromide with ethyl bromoacetate to react with N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a white solid in 38% yield: 1H NMR (300 MHz, CDCl3) δ 7.39-7.27 (m, 5H), 5.87 (t, J=5.4 Hz, 1H), 4.57 (d, J=5.4 Hz, 2H), 4.27-4.13 (m, 4H), 4.08 (s, 2H), 3.76-3.68 (m, 2H), 2.63 (s, 3H), 1.29 (t, J=7.1 Hz, 3H); MS (ES+) m/z 403.2 (M+1).

Sources & evidence

ORD record: ord-dab70fb8408e42d4a43dedf606c88a74
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

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