4-(Chloromethyl)benzonitrile → Ethyl 5-(3-(4-cyanobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

HRID 2067649Notes

Reaction equation

HRID 2067649 reaction equation
BrCCO[Si](C(C)(C)C)(C)C.Cl[CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.[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]>>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([CH2:13][N:30]2[CH2:31][CH2:32][N:28]([C:26]3[S:25][C:24]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:23]([CH3:22])[CH:27]=3)[C:29]2=[O:33])=[CH:15][CH:16]=1)#[N:19]

Participants

4

Reactant 3

HCID 701274-(Chloromethyl)benzonitrileHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 58031554Ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 58031419Ethyl 5-(3-(4-cyanobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylateYield 86%

Procedure

Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with 4-(chloromethyl)benzonitrile to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as a cream solid in 86% yield: 1H NMR (300 MHz, CDCl3) δ 7.66 (d, J=8.1 Hz, 2H), 7.43 (d, J=8.1 Hz, 2H), 6.18 (s, 1H), 4.53 (s, 2H), 4.28 (q, J=7.1 Hz, 2H), 3.89-3.81 (m, 2H), 3.52-3.43 (m, 2H), 2.50 (s, 3H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 370.2 (M+1).

Sources & evidence

ORD record
ord-a679265f83d349ffabb8d89db8e55a78
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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