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

HRID 359858Notes

Reaction equation

HRID 359858 reaction equation
[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

Participants

5

Reactant 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

Product 1

HCID 441048Win 54954Yield 66%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b4a382e3217f4652947ed70e44a70ab0
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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