4-(Chloromethyl)benzonitrile → HCID 25096192, compound

HRID 2067554Notes

Reaction equation

HRID 2067554 reaction equation
ClCC1C=CC(C#N)=CC=1.Br[CH2:12][C:13]1[O:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=1.[CH2:22]([NH:29][C:30]([C:32]1[S:36][C:35]([N:37]2[CH2:41][CH2:40][NH:39][C:38]2=[O:42])=[N:34][C:33]=1[CH3:43])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([NH:29][C:30]([C:32]1[S:36][C:35]([N:37]2[CH2:41][CH2:40][N:39]([CH2:12][C:13]3[O:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=3)[C:38]2=[O:42])=[N:34][C:33]=1[CH3:43])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 701274-(Chloromethyl)benzonitrileHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 59481185N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 25096192HCID 25096192, compoundYield 27%

Procedure

Following the procedure as described in Example 23, making variations as required to replace 4-(chloromethyl)benzonitrile with 2-(bromomethyl)-5-(trifluoromethyl)furan 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 27% yield: mp 143-145° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.35-7.28 (m, 5H), 6.76-6.75 (m, 1H), 6.39 (d, J=3.0 Hz, 1H), 5.90 (t, J=6.0 Hz, 1H), 4.57 (d, J=6.0 Hz, 2H), 4.51 (s, 2H), 4.11 (t, J=9.0 Hz, 2H), 3.64 (t, J=9.0 Hz, 2H), 2.62 (s, 3H); MS (ES+) m/z 465.3 (M+1).

Sources & evidence

ORD record
ord-d0e57cbb3b204ac6b69c0eafe84fd9d4
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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