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Thionyl Chloride → {2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazol-5-yl}methanol

HRID 1776990
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HRID 1776990 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:30])([F:29])[F:28])[CH2:14][CH2:13][N:12]([C:15]3[S:16][C:17]([C:24](O)=[O:25])=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].S(Cl)(Cl)=O>CN(C)C=O.ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:30])([F:28])[F:29])[CH2:14][CH2:13][N:12]([C:15]3[S:16][C:17]([CH2:24][OH:25])=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]
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참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 594533662-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid

생성물 1

HCID 59453386{2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazol-5-yl}methanol수율 65%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매
HCID 11
1,2-Dichloroethane
용매

실험 절차

2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoro-methyl)-1,3-thiazole-5-carboxylic acid (2.2 g) was added to 1,2-dichloroethane (50 mL). Thionyl chloride (1.0 g) and one drop of N,N-dimethylformamide were added to the mixture, which was then refluxed under heating for 5 hours. After removing the solvent by evaporation, the residues were dissolved in 1,4-dioxane (20 mL), and then added dropwise to the mixture solution comprising water (30 mL), 1,4-dioxane (30 mL), and sodium borohydride (0.5 g) under ice cooling. After the dropwise addition was completed, the reaction solution was refluxed under heating for one hour. After cooling, the reaction solution was poured over ice water, and then extracted with ethyl acetate. After cooling, the extraction was again carried out by adding water and 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 (1.1 g, 65%).

후처리

  1. temperaturewas then refluxed
  2. temperatureunder heating for 5 hours
  3. customAfter removing the solvent
  4. customby evaporation
  5. dissolutionthe residues were dissolved in 1,4-dioxane (20 mL)
  6. additionadded dropwise to the mixture solution comprising water (30 mL), 1,4-dioxane (30 mL), and sodium borohydride (0.5 g) under ice cooling
  7. additionAfter the dropwise addition
  8. temperaturethe reaction solution was refluxed
  9. temperatureunder heating for one hour
  10. temperatureAfter cooling
  11. additionthe reaction solution was poured over ice water
  12. extractionextracted with ethyl acetate
  13. temperatureAfter cooling
  14. extractionthe extraction
  15. additionby adding water and ethyl acetate
  16. dry with materialThe organic layer was dried over magnesium sulfate
  17. customThe solvent was evaporated off under reduced pressure
  18. customthe residue was then purified by a silica gel chromatography

출처 및 근거

ORD 기록
ord-c13b9bd52347422fa51473c9d26b27e9
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266830B2

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