4-(Chloromethyl)benzonitrile → HCID 25096449, compound

HRID 560783Notes

Reaction equation

HRID 560783 reaction equation
ClCC1C=CC(C#N)=CC=1.Br[CH2:12][CH:13]1[O:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[O:15][CH2:14]1.[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][CH:13]3[O:18][C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[O:15][CH2:14]3)[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 983332-Bromomethyl-1,4-benzodioxaneHCID 59481185N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 25096449HCID 25096449, compoundYield 3%

Procedure

Following the procedure as described in Example 23, making variations as required to replace 4-(chloromethyl)benzonitrile with 2-(bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine to react with N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as an oil in 3% yield: 1H NMR (300 MHz, CDCl3) δ 7.35-7.31 (m, 5H), 6.88-6.87 (m, 4H), 5.89 (br s, 1 H), 4.57 (d, J=6.0 Hz, 2H), 4.43-4.39 (m, 1H), 4.33-4.28 (m, 1H), 4.17-3.97 (m, 3 H), 3.86-3.53 (m, 4H), 2.63 (s, 3H); MS (ES+) m/z 465.2 (M+1).

Sources & evidence

ORD record
ord-0f18912d63f546b3a6ee6e3c54b9c473
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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