1-Chloro-4-(chloromethyl)benzene → Ethyl 2-(3-(4-chlorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 560680Notes

Reaction equation

HRID 560680 reaction equation
C1(CBr)CC1.[Cl:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Cl)=[CH:9][CH:8]=1.[CH3:15][C:16]1[N:17]=[C:18]([N:26]2[CH2:30][CH2:29][NH:28][C:27]2=[O:31])[S:19][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[Cl:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][N:28]2[CH2:29][CH2:30][N:26]([C:18]3[S:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:16]([CH3:15])[N:17]=3)[C:27]2=[O:31])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81503BromomethylcyclopropaneHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031538Ethyl 2-(3-(4-chlorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 84%

Procedure

Following the procedure as described in Example 10, making variations as required to replace cyclopropylmethyl bromide with 4-chlorobenzyl chloride to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 84% yield: mp 117-119° C. (ethyl acetate/hexanes): 1H NMR (300 MHZ, DMSO-d6) δ 7.31 (d, J=7.2 Hz, 2H), 7.22 (d, J=7.2 Hz, 2H), 4.51 (s, 2H), 4.27 (q, J=7.8 Hz, 2H), 4.09-4.04 (m, 2H), 3.44-3.41 (m, 2H), 2.59 (s, 3H), 1.25 (t, J=7.8 Hz, 3H): MS (ES+) m/z 380.2 (M+1), 382.2 (M+1).

Sources & evidence

ORD record
ord-43fdd291b306450eaa2cdad369270fad
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

Loading…