Toluene → 4-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole

HRID 352073

반응식

HRID 352073 반응식
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.ClCC(CCl)=O.[C:22]1([CH3:28])[CH:27]=CC=CC=1.[C:29]([O-:32])(=[O:31])[CH3:30].[Na+]>CO.CS(C)=O>[C:29]([O:32][CH2:28][C:22]1[N:13]=[C:11](/[CH:10]=[CH:9]/[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=2)[O:12][CH:27]=1)(=[O:31])[CH3:30]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 107931,3-DichloroacetoneHCID 517045Sodium AcetateHCID 57090144-(Trifluoromethyl)cinnamamide

생성물 1

HCID 129928464-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole수율 51%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 887Methanol용매

반응 조건

온도
75 °C

실험 절차

(E)-3-(4-(Trifluoromethyl)phenyl)-2-propenamide (950 g, 4.42 mol) and 1,3-dichloroacetone (1045 g, 8.23 mol)were added to toluene (4.75 L) and the mixture was subjected to refluxing azeotropic dehydration using a Dean-Stark tube for 8 hours. During the reaction, an azeotropic mixture (2.38 L) was removed. The reaction mixture was concentrated under reduced pressure, and dimethyl sulfoxide (4.75L) and sodium acetate (905 g, 11.0 mol) were added to the residue. The mixture was stirred at 70-80° C. for 3.5 hours. Methanol (4.75 L) was added. After allowing to cool to room temperature and stirring, the mixture was stirred for 1 hour under ice-cooling. The precipitated crystals were collected by filtration, washed with cold-methanol (1.9 L), and dried under reduced pressure to give 4-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (1560 g, yield 51%).

후처리

  1. temperatureto refluxing azeotropic dehydration
  2. customfor 8 hours
  3. customDuring the reaction
  4. customan azeotropic mixture (2.38 L) was removed
  5. additionwere added to the residue
  6. temperatureto cool to room temperature
  7. stirringstirring
  8. stirringthe mixture was stirred for 1 hour under ice-
  9. temperaturecooling
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with cold-methanol (1.9 L)
  12. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-87acf2d9cbc24512b9fdde5a0a549b33
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743924B2

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