Phenethyl tosylate → Ethyl 3-methyl-5-(2-oxo-3-phenethylimidazolidin-1-yl)thiophene-2-carboxylate

HRID 560691Notes

Reaction equation

HRID 560691 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.CC1C=CC(S(O[CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=O)=O)=CC=1.[CH3:32][C:33]1[CH:37]=[C:36]([N:38]2[CH2:42][CH2:41][NH:40][C:39]2=[O:43])[S:35][C:34]=1[C:44]([O:46][CH2:47][CH3:48])=[O:45]>>[CH3:32][C:33]1[CH:37]=[C:36]([N:38]2[CH2:42][CH2:41][N:40]([CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:39]2=[O:43])[S:35][C:34]=1[C:44]([O:46][CH2:47][CH3:48])=[O:45]

Participants

4

Reactant 3

HCID 20522Phenethyl tosylateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 58031554Ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 58031586Ethyl 3-methyl-5-(2-oxo-3-phenethylimidazolidin-1-yl)thiophene-2-carboxylateYield 63%

Procedure

Following the procedure as described in Example 13, making variations as required to replace 4-(trifluoromethyl)benzyl bromide with phenethyl 4-methylbenzenesulfonate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as a colorless solid in 63% yield: 1H NMR (300 MHz, CDCl3) δ 7.35-7.19 (m, 5H), 6.12 (s, 1H), 4.27 (q, J=7.1 Hz, 2H), 3.78-3.71 (m, 2H), 3.56 (t, J=7.4 Hz, 2H), 3.47-3.39 (m, 2H), 2.90 (t, J=7.4 Hz, 2H), 2.49 (s, 3H), 1.33 (t, J=7.1 Hz, 3H); MS (ES+) m/z 359.3 (M+1).

Sources & evidence

ORD record
ord-1a4491ac8da645b5a8960ccc23a6d28f
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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