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

HRID 359858ノート

反応式

HRID 359858 の反応式
[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

参加物

5

反応物 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

生成物 1

HCID 441048Win 54954収率 66%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b4a382e3217f4652947ed70e44a70ab0
出典データセット
uspto-grants-1991_03
特許番号
US05002960

反応ノート

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