Phenacyl bromide → Ethyl 3-methyl-5-(2-oxo-3-(2-oxo-2-phenylethyl)imidazolidin-1-yl)thiophene-2-carboxylate

HRID 560869Notes

Reaction equation

HRID 560869 reaction equation
BrCCO[Si](C(C)(C)C)(C)C.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].[CH3:22][C:23]1[CH:27]=[C:26]([N:28]2[CH2:32][CH2:31][NH:30][C:29]2=[O:33])[S:25][C:24]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35]>>[CH3:22][C:23]1[CH:27]=[C:26]([N:28]2[CH2:32][CH2:31][N:30]([CH2:13][C:14](=[O:15])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:29]2=[O:33])[S:25][C:24]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

4

Reactant 3

HCID 6259Phenacyl bromideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 58031554Ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 58031477Ethyl 3-methyl-5-(2-oxo-3-(2-oxo-2-phenylethyl)imidazolidin-1-yl)thiophene-2-carboxylateYield 39%

Procedure

Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with 2-bromoacetophenone to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as a colorless solid in 39% yield: 1H NMR (300 MHz, CDCl3) δ 7.95 (d, J=8.3 Hz, 2H), 7.60-7.56 (m, 1H), 7.52-7.44 (m, 2H), 6.18 (s, 1H), 4.73 (s, 2H), 4.24 (q, J=7.1 Hz, 2H), 3.94-3.86 (m, 2H), 3.76-3.68 (m, 2H), 2.48 (s, 3H), 1.30 (t, J=7.1 Hz, 3H); MS (ES+) m/z 373.2 (M+1).

Sources & evidence

ORD record
ord-62c542ad9b6e42199025fdc5a9c40ab3
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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