Benzyl Bromide → Ethyl 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 554902Notes

Reaction equation

HRID 554902 reaction equation
BrCC1CC1(F)F.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:16][C:17]1[N:18]=[C:19]([N:27]2[CH2:31][CH2:30][NH:29][C:28]2=[O:32])[S:20][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[CH2:8]([N:29]1[CH2:30][CH2:31][N:27]([C:19]2[S:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:17]([CH3:16])[N:18]=2)[C:28]1=[O:32])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 57919811Ethyl 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 93%

Procedure

Following the procedure as described in Preparation 13, making variations as required to replace bromomethyl-2,2-difluorocyclopropane with benzyl bromide to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 93% yield: mp 122-124° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.35-7.26 (m, 5H), 4.40 (s, 2H), 4.19 (q, J=7.2 Hz, 2H), 3.97 (t, J=7.5 Hz, 2H), 3.42 (t, J=7.5 Hz, 2H), 2.48 (s, 3H), 1.23 (t, J=7.2 Hz, 3H); MS (ES+) m/z 346.0 (M+1).

Workup

  1. customas described in Preparation 13

Sources & evidence

ORD record
ord-20046afbfec8471590c767b541b4c630
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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