Hydrochloric Acid → HCID 70362693, compound

HRID 2351289Notes

Reaction equation

HRID 2351289 reaction equation
[NH2:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13]Br)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[H-].[Na+].O.Cl>O1CCCC1>[CH:10]1[C:5]2[O:4][N:3]=[C:2]3[N:1]=[CH:13][CH2:12][O:11][C:7]([C:6]=23)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydride2×HCID 14836203HCID 14836203, compound

Product 1

HCID 70362693HCID 70362693, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-4-[(2-bromoethyl)oxy]1,2-benzisoxazole of Example 7(a) (10.86 g, 0.0428 mole) was dissolved in 200 ml of tetrahydrofuran (THF) and 5.0 g of NaH (50% oil dispersion, 0.10 mole) was added. The reaction mixture was brought to reflux. After 30 minutes the reaction mixture was allowed to cool, an additional 1.0 g of NaH dispersion was added, and reflux was continued for 30 minutes. At the end of this time the reaction mixture was poured into H2O, acidified with concentrated hydrochloric acid, and the product extracted into ether. The organic phase was separated, dried, and concentrated, after which the residue was purified by flash chromatography (10% ethyl acetate -CH2Cl2). The material obtained in this manner retained a little yellow color, which was removed by dissolving the compound in CH2Cl2 and passing the solution over a short column of alumina. The product obtained in this manner after concentration of the solvent was recrystallized from CH2Cl2 -pentane to give 2.20 g (29%) of 4,5-dihydroisoxazolo[3,4,5-ef][1,4]benzoxazepine, mp 165°-166° C.

Workup

  1. temperatureto reflux
  2. temperatureto cool
  3. temperaturereflux
  4. waitwas continued for 30 minutes
  5. extractionthe product extracted into ether
  6. customThe organic phase was separated
  7. customdried
  8. concentrationconcentrated
  9. customafter which the residue was purified by flash chromatography (10% ethyl acetate -CH2Cl2)
  10. customThe material obtained in this manner
  11. customwas removed
  12. dissolutionby dissolving the compound in CH2Cl2
  13. customThe product obtained in this manner after concentration of the solvent
  14. customwas recrystallized from CH2Cl2 -pentane

Sources & evidence

ORD record
ord-610cfe8a7c414d3ca884eccd2b1374ad
Source dataset
uspto-grants-1989_10
Patent number
US04873234

Reaction notes

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