1,8-Diazabicyclo(5.4.0)undec-7-ene → Win 54954

HRID 359858노트

반응식

HRID 359858 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([Cl:26])[C:13]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[O:24][N:23]=[C:22]([CH3:25])[CH:21]=1)[C:5]([NH:7][CH2:8][CH2:9]Cl)=[O:6].N12CCCN=C1CCCCC2>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH2:9][CH2:8][N:7]=2)[CH:11]=[C:12]([Cl:26])[C:13]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[O:24][N:23]=[C:22]([CH3:25])[CH:21]=1

참가 물질

5

반응물 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 200640513,5-dichloro-N-(2-chloroethyl)-4-{[5-(3-methyl-5-isoxazolyl)pentyl]oxy}benzamide

생성물 1

HCID 441048Win 54954수율 66%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1.0 g 3,5-dichloro-N-(2-chloroethyl)-4-{[5-(3-methyl-5-isoxazolyl)pentyl]oxy}benzamide in 75 ml methylene dichloride was added 0.92 g 1,8-diazabicyclo[5.4.0]undec-7-ene, and the mixture was heated at reflux for about 16 hrs. The reaction mixture was concentrated in vacuo and the residue partitioned between 150 ml ethyl acetate and 50 ml water. The organic layer was separated, washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel and eluted with 1:1 ethyl acetate:hexane. The eluted material was isolated, dissolved in ether and crystallized upon seeding to give 0.60 g (66%) of 5-{5-[2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole, light yellow solid, m.p. 39°-40° C., identical with the compound of Example 105, as confirmed by thin layer chromatography.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for about 16 hrs
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between 150 ml ethyl acetate and 50 ml water
  5. customThe organic layer was separated
  6. washwashed with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washeluted with 1:1 ethyl acetate
  11. customThe eluted material was isolated
  12. customcrystallized

출처 및 근거

ORD 기록
ord-b4a382e3217f4652947ed70e44a70ab0
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05002960

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