1-(Bromomethyl)-4-(trifluoromethyl)benzene → ethyl 4-methyl-2-(5-oxo-1-(4,4,4-trifluorobutyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

HRID 560745Notes

Reaction equation

HRID 560745 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9]C(CBr)=CC=1.BrCCCC(F)(F)F.[CH3:21][C:22]1[N:23]=[C:24]([N:32]2[C:36](=[O:37])[NH:35][N:34]=[CH:33]2)[S:25][C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]>>[CH3:21][C:22]1[N:23]=[C:24]([N:32]2[C:36](=[O:37])[N:35]([CH2:9][CH2:10][CH2:3][C:2]([F:1])([F:11])[F:12])[N:34]=[CH:33]2)[S:25][C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

4

Reactant 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 57920013ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

Product 1

HCID 58031433ethyl 4-methyl-2-(5-oxo-1-(4,4,4-trifluorobutyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylateYield 32%

Procedure

Following the procedure as described in Example 19, making variation as required to replace 4-(trifluoromethyl)benzyl bromide with 4-bromo-1,1,1-trifluorobutane to react with ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate, the title compound was obtained as a white solid in 32% yield: 1H NMR (300 MHz, CDCl3) δ 8.28 (s, 1H), 4.29 (q, J=7.1 Hz, 2H), 3.92 (t, J=6.6 Hz, 2H), 2.64 (s, 3H), 2.99-1.96 (m, 4H), 1.35 (t, J=7.1 Hz, 3H); MS (ES+) m/z 365.3 (M+1).

Sources & evidence

ORD record
ord-7c45edffdb2f461582a41a61733ff24e
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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