1-(Bromomethyl)-4-(trifluoromethyl)benzene → Ethyl 2-(3-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 2067472Notes

Reaction equation

HRID 2067472 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][C:15]1[CH:23]=[CH:22][C:18]2=[N:19][O:20][N:21]=[C:17]2[CH:16]=1.[CH3:24][C:25]1[N:26]=[C:27]([N:35]2[CH2:39][CH2:38][NH:37][C:36]2=[O:40])[S:28][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[N:19]1[O:20][N:21]=[C:17]2[CH:16]=[C:15]([CH2:14][N:37]3[CH2:38][CH2:39][N:35]([C:27]4[S:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:25]([CH3:24])[N:26]=4)[C:36]3=[O:40])[CH:23]=[CH:22][C:18]=12

Participants

4

Reactant 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 27355875-(Bromomethyl)-2,1,3-benzoxadiazoleHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031450Ethyl 2-(3-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 92%

Procedure

Following the procedure as described in Example 13, making variations as required to replace 4-(trifluoromethyl)benzyl bromide with 5-(bromomethyl)benzo[c]-[1,2,5]oxadiazole to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained as a colorless solid in 92% yield: MS (ES+) m/z 388.1 (M+1).

Sources & evidence

ORD record
ord-5eb2f6f8d4a741d886b7813b8ff79320
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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