Hydrochloric Acid → HCID 5325766, compound

HRID 2165903Notes

Reaction equation

HRID 2165903 reaction equation
[C:1]1([C:7]2[C:11]3[C:12](=O)[CH2:13][CH2:14][CH2:15][C:10]=3[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCl.[N-:20]=[N+]=[N-].[Na+].Cl>OS(O)(=O)=O>[N:8]1[O:9][C:10]2[CH2:15][CH2:14][CH2:13][C:12]3[C:11]=2[C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:20]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 33557Sodium AzideHCID 12344070HCID 12344070, compound

Product 1

HCID 5325766HCID 5325766, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3-Phenyl-4-oxo-4,5,6,7-tetrahydrobenz[1,2-d]isoxazole (6.0 g) was dissolved in 40 ml conc. H2SO4 and then dichloromethane (60 ml) was added. NaN3 (2.0 g) was added portionwise at such a rate that foaming could be controlled. After 90 minutes, the reaction mixture was poured into ice/water and conc. HCl was added until the precipitated amine sulfate dissolved. The dichloromethane layer was separated and the aqueous phase was washed with additional dichloromethane. The aqueous phase was made basic with 50% NaOH and ice (up to pH 1-4) and then with NaHCO3 (up to pH 8). The product was extracted into dichloromethane and then flushed over a short alumina column before concentration under reduced pressure. Recrystallization from EtOAc/hexane gave 1.85 g of product, m.p. 149°-150° C.

Workup

  1. dissolutiondissolved
  2. customThe dichloromethane layer was separated
  3. washthe aqueous phase was washed with additional dichloromethane
  4. extractionThe product was extracted into dichloromethane
  5. customflushed over a short alumina column before concentration under reduced pressure
  6. customRecrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-9bbf2836c78b4a0a9fe6fec7acffc588
Source dataset
uspto-grants-1990_07
Patent number
US04942237

Reaction notes

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