Epichlorohydrin → HCID 13038067, compound

HRID 1759332Notes

Reaction equation

HRID 1759332 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[CH2:12]([CH:14]1O[CH2:15]1)[Cl:13].C(P(=[O:30])(CCCC)CCCC)CCC.[Br-].[Li+]>C1(C)C(C)=CC=CC=1>[Cl:13][CH2:12][CH:14]1[O:11][C:10](=[O:30])[N:9]([C:6]2[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)[CH2:15]1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 13138Tributylphosphine oxideHCID 82050Lithium BromideHCID 27333164-(Methylthio)phenyl isocyanate

Product 1

HCID 13038067HCID 13038067, compoundYield 192%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

To a hot (130° C.) solution of 105 g (0.64 mole) of 4-methylthiophenyl isocyanate and 93 g (1 mole) of epichlorohydrin in 600 ml of xylene was added 200 ml of tri-n-butylphosphine oxide-lithium bromide complex. (The complex was prepared by heating a mixture of 45 g of tri-n-butylphosphine oxide, 12.7 g of lithium bromide and 550 ml of xylene to reflux until a clear solution was obtained by removing water.) An exothermic reaction took place. After all of the catalyst had been added, the mixture was heated under reflux for 1 hour and cooled. The solution was decanted into a flask and concentrated to one-half the volume. An equal volume of petroleum ether was added to the residue. The solid that formed was collected by filtration and recrystallized from acetonitrile to give 102 g (62% yield) of the title compound; m.p. 106.5°-107.5° C.

Workup

  1. custom(The complex was prepared
  2. temperatureby heating
  3. temperatureto reflux until a clear solution
  4. customwas obtained
  5. customby removing water
  6. custom) An exothermic reaction
  7. additionAfter all of the catalyst had been added
  8. temperaturethe mixture was heated
  9. temperatureunder reflux for 1 hour
  10. temperaturecooled
  11. customThe solution was decanted into a flask
  12. concentrationconcentrated to one-half the volume
  13. additionAn equal volume of petroleum ether was added to the residue
  14. customThe solid that formed
  15. filtrationwas collected by filtration
  16. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-0a2e95744a134c80a6d732b068fb9399
Source dataset
uspto-grants-1982_07
Patent number
US04340606

Reaction notes

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