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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
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HRID 1776988 반응식
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]
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HCID 11430Potassium CarbonateHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylateHCID 594533723-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidine

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-53437cd73c6d4e55a02fa04595183111
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266830B2

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