Tetrahydrofuran → HCID 21421202, compound

HRID 259305Notes

Reaction equation

HRID 259305 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[O:6][CH2:7][CH:8]([OH:11])[CH2:9][NH2:10])#[N:2].O1CCCC1.C(=O)(O)[O-].[Na+].[C:25](Br)([CH3:28])([CH3:27])[CH3:26]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[O:6][CH2:7][CH:8]([OH:11])[CH2:9][NH:10][C:25]([CH3:28])([CH3:27])[CH3:26])#[N:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10485t-Butyl bromideHCID 516892Sodium BicarbonateHCID 21421184HCID 21421184, compound

Product 1

HCID 21421202HCID 21421202, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.6 gm (0.05 mol) of 1-(3-cyanophenoxy)-2-hydroxy-3-amino propane were dissolved in 40 ml of dimethylformamide and 100 ml of tetrahydrofuran and 4.2 gm (0.05 mol) of pulverized sodium bicarbonate were added thereto. Then, 6.9 gm (0.05 mol) of tert.-butylbromide were added and the mixture was refluxed for 24 hours. After the mixture had been cooled, the inorganic solid was filtered off and the solvent mixture was distilled off in vacuo. The residue was dissolved by heating in ethyl acetate and the insoluble inorganic portions were vacuum filtered off and the filtrate was admixed with petroleum ether. The base precipitated in solid form and was isolated and recrystallized from ethyl acetate with an addition of petroleum ether to obtain 1-(3-cyanophenoxy)-2-hydroxy-3-tert.-butylamino propane having a melting point of 108°-110° C.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperatureAfter the mixture had been cooled
  3. filtrationthe inorganic solid was filtered off
  4. distillationthe solvent mixture was distilled off in vacuo
  5. dissolutionThe residue was dissolved
  6. temperatureby heating in ethyl acetate
  7. filtrationfiltered off
  8. customThe base precipitated in solid form
  9. customwas isolated
  10. customrecrystallized from ethyl acetate with an addition of petroleum ether

Sources & evidence

ORD record
ord-df94d3d6fc664722b8baccc88d84a286
Source dataset
uspto-grants-1977_07
Patent number
US04036988

Reaction notes

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