4-(Chloromethyl)benzonitrile → HCID 59481211, compound

HRID 560776Notes

Reaction equation

HRID 560776 reaction equation
ClCC1C=CC(C#N)=CC=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20].[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([N:38]2[CH2:42][CH2:41][NH:40][C:39]2=[O:43])=[N:35][C:34]=1[CH3:44])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([N:38]2[CH2:42][CH2:41][N:40]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[C:39]2=[O:43])=[N:35][C:34]=1[CH3:44])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 701274-(Chloromethyl)benzonitrileHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 59481185N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 59481211HCID 59481211, compoundYield 34%

Procedure

Following the procedure as described in Example 23, making variations as required to replace 4-(chloromethyl)benzonitrile with 1-(bromomethyl)-2-(trifluoromethyl)benzene to react with N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 34% yield: mp 138-140° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.67-7.65 (m, 1H), 7.59-7.46 (m, 2H), 7.42-7.27 (m, 6H), 5.89 (t, J=5.5 Hz, 1H), 4.68 (s, 2H), 4.56 (d, J=5.5 Hz, 2H), 4.11-4.05 (m, 2H), 3.49-3.43 (m, 2H), 2.61 (s, 3H); 13C NMR (75 MHz, CDCl3); 162.3, 157.2, 155.7, 153.2, 137.9, 134.7, 132.5, 130.0, 128.8, 127.8, 126.1, 125.9, 122.3, 117.4, 44.0, 43.9, 42.0, 41.9, 17.2; MS (ES+) m/z 475.3 (M+1).

Sources & evidence

ORD record
ord-28e911030409455da5904df9afd68be2
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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