3,5-Dichloro-1,2-benzoxazole → HCID 23368515, compound

HRID 1901593Notes

Reaction equation

HRID 1901593 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][OH:14])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Cl[C:24]1[C:28]2[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=2[O:26][N:25]=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][O:14][C:24]2[C:28]3[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=3[O:26][N:25]=2)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 135684483,5-Dichloro-1,2-benzoxazoleHCID 14409442Tert-butyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 23368515HCID 23368515, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 6.94 g of 3-tert-butoxycarbonyl-4-hydroxymethyl-2,2-dimethyloxazolidine in 28 ml of tetrahydrofuran is added to a solution of 6.02 g of potassium tert-butoxide in 28 ml of tetrahydrofuran at 10°-15° C., and they are subjected to reaction at the same temperature for two hours. Subsequently, this reaction mixture is added under reflux to a solution of 5.64 g of 3,5-dichloro-1,2-benzoisoxazole in 28 ml of tetrahydrofuran and they are refluxed for a further one hour. The reaction mixture is cooled and thereafter the solvent is removed by distillation under reduced pressure, after which 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 crystals obtained are recrystallized from n-hexane to obtain 8.41 g of colorless, crystalline 3-[(3-tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methoxy]-5-chloro-1,2-benzoisoxazole having a melting point of 117°-118° C.

Workup

  1. customthey are subjected to reaction at the same temperature for two hours
  2. additionSubsequently, this reaction mixture is added
  3. temperatureare refluxed for a further one hour
  4. temperatureThe reaction mixture is cooled
  5. customthe solvent is removed by distillation under reduced pressure
  6. additionafter which ethyl acetate and water are added to the residue
  7. customobtained
  8. customthe organic layer is separated
  9. washThe separated organic layer is washed with a saturated saline solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customafter which the solvent is removed by distillation under reduced pressure
  12. customThe crystals obtained
  13. customare recrystallized from n-hexane

Sources & evidence

ORD record
ord-d35acc79837d47d182b37ddf528ae87b
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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