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

HRID 560581Notes

Reaction equation

HRID 560581 reaction equation
C(Br)C1C=CC=CC=1.[F:9][CH:10]([F:20])[O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.[CH3:21][C:22]1[N:23]=[C:24]([N:32]2[CH2:36][CH2:35][NH:34][C:33]2=[O:37])[S:25][C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]>>[F:9][CH:10]([F:20])[O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:34]2[CH2:35][CH2:36][N:32]([C:24]3[S:25][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:22]([CH3:21])[N:23]=3)[C:33]2=[O:37])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 27370014-(Difluoromethoxy)benzyl BromideHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031483Ethyl 2-(3-(4-(difluoromethoxy)benzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 88%

Procedure

Following the procedure as described in Example 5, making variations to replace benzyl bromide with 4-(difluoromethoxy)benzyl bromide to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 88% yield: 1H NMR (300 MHz, DMSO-d6) δ 7.37 (d, J=8.1 Hz, 2H), 7.29 (d, J=8.1 Hz, 2H), 6.48 (t, JF-H=73.8 Hz, 1H), 4.46 (s, 2H), 4.26 (q, J=7.2 Hz, 2H), 4.07 (t, J=7.8 Hz, 2H), 3.45 (t, J=7.8 Hz, 2H), 2.56 (s, 3H), 1.30 (t, J=7.2 Hz, 3H); MS (ES+) m/z 412.2 (M+1).

Sources & evidence

ORD record
ord-85a10919972343bda9646896b8606e49
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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