1-(Bromomethyl)-4-(trifluoromethyl)benzene → Ethyl 4-methyl-2-(3-((3-methyl-5-phenylisoxazol-4-yl)methyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

HRID 560696Notes

Reaction equation

HRID 560696 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][C:15]1[C:16]([CH3:26])=[N:17][O:18][C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:27][C:28]1[N:29]=[C:30]([N:38]2[CH2:42][CH2:41][NH:40][C:39]2=[O:43])[S:31][C:32]=1[C:33]([O:35][CH2:36][CH3:37])=[O:34]>>[CH3:27][C:28]1[N:29]=[C:30]([N:38]2[CH2:42][CH2:41][N:40]([CH2:14][C:15]3[C:16]([CH3:26])=[N:17][O:18][C:19]=3[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:39]2=[O:43])[S:31][C:32]=1[C:33]([O:35][CH2:36][CH3:37])=[O:34]

Participants

4

Reactant 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 27765184-(bromomethyl)-3-methyl-5-phenylisoxazoleHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031639Ethyl 4-methyl-2-(3-((3-methyl-5-phenylisoxazol-4-yl)methyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylateYield 87%

Procedure

Following the procedure as described in Example 13, making variations as required to replace 4-(trifluoromethyl)benzyl bromide with 4-(bromomethyl)-3-methyl-5-phenylisoxazole to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained as a colorless solid in 87% yield: MS (ES+) m/z 427.2 (M+1).

Sources & evidence

ORD record
ord-6c6fbb5adc6346a69265dc5b3afd9e7f
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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