Acetic Acid → 1-(4-Chlorophenyl)-2-(3-(Trifluoromethyl)-5-Isothiazolyl)Ethanone

HRID 36944

反応式

HRID 36944 の反応式
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:3].CS([C:15]1[S:19][N:18]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:16]=1)(=O)=O.C(O)(=O)C>O1CCCC1>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][C:15]2[S:19][N:18]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:16]=2)=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 7467P-ChloroacetophenoneHCID 152392145-Methylsulfonyl-3-(trifluoromethyl)isothiazole

生成物 1

HCID 152392151-(4-Chlorophenyl)-2-(3-(Trifluoromethyl)-5-Isothiazolyl)Ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The oil of a 4.0 g (100 mmol) portion of 60 percent in mineral oil sodium hydride was removed by triple extraction with hexane and was replaced with 100 mL of tetrahydrofuran. 4-Chloroacetophenone (4.33 g, 28 mmol) was added and the mixture was heated at reflux with stirring for 1 hr and then allowed to cool. 5-Methylsulfonyl-3-(trifluoromethyl)isothiazole (4.57 g, 19.8 mmol) dissolved in a small amount of tetrahydrofuran was added and the mixture was heated at reflux with stirring for 3 hr and then allowed to cool. The mixture was next acidified with 60 mL of 10 percent aqueous acetic acid and the layers that formed were separated. The aqueous layer was extracted with 2×100 mL of ether and the organic fractions were combined, washed with aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a residue. This residue was washed with hexane and crystallized from a 1:1 mixture of dichloromethane and hexane to obtain 3.19 g (53 percent of theory) of the title compound as a solid melting at 109°-110° C.

後処理

  1. customThe oil of a 4.0 g (100 mmol) portion of 60 percent in mineral oil sodium hydride was removed by triple extraction with hexane
  2. temperaturethe mixture was heated
  3. temperatureat reflux
  4. temperatureto cool
  5. additionwas added
  6. temperaturethe mixture was heated
  7. temperatureat reflux
  8. stirringwith stirring for 3 hr
  9. temperatureto cool
  10. customthe layers that formed
  11. customwere separated
  12. extractionThe aqueous layer was extracted with 2×100 mL of ether
  13. washwashed with aqueous sodium bicarbonate solution
  14. dry with materialdried over sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated by evaporation under reduced pressure
  17. customto obtain a residue
  18. washThis residue was washed with hexane
  19. customcrystallized from a 1:1 mixture of dichloromethane and hexane

出典と根拠

ORDレコード
ord-623b39e3a6bc4ee7baac5979b7b7ec69
出典データセット
uspto-grants-1995_05
特許番号
US05418247

関連ノート

読み込み中…