Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate → 4-Methyl-2-(2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

HRID 560604Notes

Reaction equation

HRID 560604 reaction equation
CC1N=C(N2CCN(C3C=CC=CC=3)C2=O)SC=1C(OCC)=O.[CH3:24][C:25]1[N:26]=[C:27]([N:35]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:36]2=[O:49])[S:28][C:29]=1[C:30]([O:32]CC)=[O:31]>>[CH3:24][C:25]1[N:26]=[C:27]([N:35]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:36]2=[O:49])[S:28][C:29]=1[C:30]([OH:32])=[O:31]

Participants

3

Reactant 2

HCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylateHCID 58031520Ethyl 4-methyl-2-(2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 580314644-Methyl-2-(2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl)thiazole-5-carboxylic acidYield 99%

Procedure

Following the procedure as described in Example 6, making variations as required to replace ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate with ethyl 4-methyl-2-(2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 99% yield: mp 218-221° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.25-7.10 (m, 5H), 3.94-3.89 (m, 2H), 3.53-3.48 (m, 2H), 3.22 (t, J=6.9 Hz, 2H), 2.55 (t, J=7.5 Hz, 2H), 2.46 (s, 3H), 1.83-1.73 (m, 2H); MS (ES+) m/z 346.2 (M+1).

Sources & evidence

ORD record
ord-a2d21c38323948259e0781742237db83
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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