Benzyl Bromide → Methyl 4-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate

HRID 2067360Notes

Reaction equation

HRID 2067360 reaction equation
C(Br)C1C=CC=CC=1.Br[CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.[C:21]([C:24]1[S:28][C:27]([N:29]2[CH2:33][CH2:32][NH:31][C:30]2=[O:34])=[N:26][C:25]=1[CH3:35])(=[O:23])[CH3:22]>>[C:21]([C:24]1[S:28][C:27]([N:29]2[CH2:33][CH2:32][N:31]([CH2:10][C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)[C:30]2=[O:34])=[N:26][C:25]=1[CH3:35])(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 579197381-(5-Acetyl-4-methylthiazol-2-yl)imidazolidin-2-one

Product 1

HCID 58031622Methyl 4-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoateYield 60%

Procedure

Following the procedure as described in Example 5, making variations to replace benzyl bromide with methyl 4-(bromomethyl)benzoate to react with 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one, the title compound was obtained in 60% yield: mp 174-175° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.02 (d, J=7.5 Hz, 2H), 7.35 (d, J=7.5 Hz, 2H), 4.53 (s, 2H), 4.12-4.03 (m, 2H), 3.96 (s, 3H), 3.49-3.44 (m, 2H), 2.60 (s, 3H), 2.39 (s, 3H); MS (ES+) m/z 374.1 (M+1).

Sources & evidence

ORD record
ord-9debfc1acf8a46218689af963281d8ee
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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