Potassium Carbonate → Ethyl 2-[3-(3,4,5-trichlorophenyl)-3-(trifluoro-methyl)pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

HRID 1776988Notes

Reaction equation

Cl[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[Cl:16][C:17]1[CH:18]=[C:19]([C:25]2([C:30]([F:33])([F:32])[F:31])[CH2:29][CH2:28][NH:27][CH2:26]2)[CH:20]=[C:21]([Cl:24])[C:22]=1[Cl:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:16][C:17]1[CH:18]=[C:19]([C:25]2([C:30]([F:33])([F:32])[F:31])[CH2:29][CH2:28][N:27]([C:2]3[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=3)[CH2:26]2)[CH:20]=[C:21]([Cl:24])[C:22]=1[Cl:23]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate (1.4 g) [see J. Het. Chem., 22, 1621 (1985)], 3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidine (1.7 g), and potassium carbonate (0.8 g) were added to N,N-dimethylformamide (50 mL), followed by heating at 100° C. for five hours. After cooling, the reaction solution was poured over ice water, and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was then purified by a silica gel chromatography to obtain the title compound (2.5 g, 86%).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
customThe solvent was evaporated off under reduced pressure
customthe residue was then purified by a silica gel chromatography

Sources & evidence

ORD record: ord-53437cd73c6d4e55a02fa04595183111
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266830B2

Reaction notes

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