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

HRID 1776988
Notes
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Reaction equation

HRID 1776988 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylateHCID 594533723-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidine

Product 1

HCID 59453365Ethyl 2-[3-(3,4,5-trichlorophenyl)-3-(trifluoro-methyl)pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazole-5-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes