N,N,N',N'-Tetramethylethylenediamine → HCID 19068203, compound

HRID 1957526Notes

Reaction equation

HRID 1957526 reaction equation
Br[CH:2]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][N:5]=1)[CH3:3].[C:13]([O-:16])(=[O:15])[CH3:14].[K+].CN(CCN(C)C)C>C(#N)C>[C:13]([O:16][CH:2]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][N:5]=1)[CH3:3])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 517044Potassium AcetateHCID 19068194HCID 19068194, compound

Product 1

HCID 19068203HCID 19068203, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.6 g of 3-(1-bromoethyl)-1,2-benzisoxazole, 2.4 g of potassium acetate, 2.1 g of N,N,N,N-tetramethylethylenediamine and 50 ml of acetonitrile are refluxed for 14 h. After cooling and filtering the mixture, the filtrate is concentrated under vacuum and diluted with diethyl ether. The ether phase is washed once with water, then twice with a 10% solution of hydrochloric acid and finally washed once with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated. The crude product is purified by chromatography over silica gel with ethyl acetate/hexane (1:3) to give 3-(1-acetoxyethyl)-1,2-benzisoxazole having a refractive index nD20 of 1.5229.

Workup

  1. temperatureare refluxed for 14 h
  2. temperatureAfter cooling
  3. filtrationfiltering the mixture
  4. concentrationthe filtrate is concentrated under vacuum
  5. additiondiluted with diethyl ether
  6. washThe ether phase is washed once with water
  7. washtwice with a 10% solution of hydrochloric acid and finally washed once with a saturated solution of sodium chloride
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe crude product is purified by chromatography over silica gel with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-61f2c0c4c9ad49878dcaa0352a6a621c
Source dataset
uspto-grants-1998_07
Patent number
US05786374

Reaction notes

Loading…