Methyl iodide → 5-Chloro-3-(3-methoxy-2-tritylaminopropoxy)-1,2-benzoisoxazole

HRID 1901601Notes

Reaction equation

HRID 1901601 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][N:10]=[C:9]([O:12][CH2:13][CH:14]([NH:17][C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][OH:16])[C:8]=2[CH:37]=1.[CH3:38]I>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][N:10]=[C:9]([O:12][CH2:13][CH:14]([NH:17][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:15][O:16][CH3:38])[C:8]=2[CH:37]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 233684925-Chloro-3-(2-tritylamino-3-hydroxypropoxy)-1,2-benzoisoxazole

Product 1

HCID 233685175-Chloro-3-(3-methoxy-2-tritylaminopropoxy)-1,2-benzoisoxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.44 g of 60% (w/w) sodium hydride in 49 ml of tetrahydrofuran is added 4.85 g of 5-chloro-3-(2-tritylamino-3-hydroxypropoxy)-1,2-benzoisoxazole at 20°-25° C. and they are refluxed for one hour. The reaction mixture is cooled to 5°-10° C., and thereafter, 1.56 g of methyl iodide is added, after which they are subjected to reaction at 20°-25° C. for five hours. The solvent is removed from the reaction mixture by distillation under reduced pressure, ethyl acetate and water are added to the residue obtained, and after shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The residue obtained is crystallized from n-hexane and the crystals are collected by filtration, to obtain 5-chloro-3-(3-methoxy-2-tritylaminopropoxy)-1,2-benzoisoxazole.

Workup

  1. temperaturethey are refluxed for one hour
  2. temperatureThe reaction mixture is cooled to 5°-10° C.
  3. customafter which they are subjected to reaction at 20°-25° C. for five hours
  4. customThe solvent is removed from the reaction mixture by distillation under reduced pressure, ethyl acetate and water
  5. additionare added to the residue
  6. customobtained
  7. customthe organic layer is separated
  8. washThe separated organic layer is washed with a saturated saline solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customafter which the solvent is removed by distillation under reduced pressure
  11. customThe residue obtained
  12. customis crystallized from n-hexane
  13. filtrationthe crystals are collected by filtration

Sources & evidence

ORD record
ord-6c2f105ac54e4e918007de84d3b7a140
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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