4-(Chloromethyl)benzonitrile → HCID 59481290, compound

HRID 560780Notes

Reaction equation

HRID 560780 reaction equation
ClCC1C=CC(C#N)=CC=1.Br[CH2:12][C:13]1[N:17]=[C:16]([CH3:18])[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]=1.[CH2:25]([NH:32][C:33]([C:35]1[S:39][C:38]([N:40]2[CH2:44][CH2:43][NH:42][C:41]2=[O:45])=[N:37][C:36]=1[CH3:46])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([NH:32][C:33]([C:35]1[S:39][C:38]([N:40]2[CH2:44][CH2:43][N:42]([CH2:12][C:13]3[N:17]=[C:16]([CH3:18])[N:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:14]=3)[C:41]2=[O:45])=[N:37][C:36]=1[CH3:46])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 701274-(Chloromethyl)benzonitrileHCID 59481185N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamideHCID 666314663-(Bromomethyl)-5-methyl-1-phenyl-1H-1,2,4-triazole

Product 1

HCID 59481290HCID 59481290, compoundYield 17%

Procedure

Following the procedure as described in Example 23, making variations as required to replace 4-(chloromethyl)benzonitrile with 3-(bromomethyl)-5-methyl-1-phenyl-1H-1,2,4-triazole 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 17% yield: mp 139-141° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.98 (d, J=8.3 Hz, 2H), 7.49-7.29 (m, 8H), 5.88 (s, 1H), 4.62 (s, 2H), 4.57 (d, J=5.6 Hz, 2H), 4.13-4.08 (m, 2H), 3.68-3.62 (m, 2H), 2.63 (s, 3H), 2.41 (s, 3H); MS (ES+) m/z 488.3 (M+1).

Sources & evidence

ORD record
ord-bf044912668046868a5351c51cc483dd
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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