Methane → HCID 86744419, compound

HRID 1111040Notes

Reaction equation

HRID 1111040 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[CH2:9]([O:12][C:13](=[O:19])[C@H:14]([CH:16]([CH3:18])[CH3:17])[NH2:15])[CH:10]=[CH2:11].C>O1CCOCC1>[N-:15]=[C:4]=[O:3].[CH2:9]([O:12][C:13](=[O:19])[C@H:14]([CH:16]([CH3:17])[CH3:18])[NH2:15])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 297MethaneHCID 10426DiphosgeneHCID 7018865HCID 7018865, compound

Product 1

HCID 86744419HCID 86744419, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.35 mol diphosgene is added dropwise over 1 hour to a mixture of 0.28 mol of valine allyl ester, prepared as described by H. Waldmann and H. Kunz in Liebigs Ann. Chem., 1983, 1712-1725, and 0.4 g activated charcoal in 400 mL dioxane under N2. The reaction mixture is then heated and stirred at reflux for 21/2 hours. The reaction mixture is then cooled, filtered, and concentrated to dryness by rotary evaporator, keeping exposure to moisture to a minimum. The crude product is re-dissolved in 100 mL THF, and the pH of the solution is adjusted to 5.5-6.0 by addition of pyridine. The product mixture is again filtered, and the product is purified by fractional distillation to give valine allyl ester isocyanate.

Workup

  1. customprepared
  2. temperatureThe reaction mixture is then heated
  3. temperatureat reflux for 21/2 hours
  4. temperatureThe reaction mixture is then cooled
  5. filtrationfiltered
  6. concentrationconcentrated to dryness by rotary evaporator
  7. dissolutionThe crude product is re-dissolved in 100 mL THF
  8. additionthe pH of the solution is adjusted to 5.5-6.0 by addition of pyridine
  9. filtrationThe product mixture is again filtered
  10. distillationthe product is purified by fractional distillation

Sources & evidence

ORD record
ord-67582a3c8eac4d59b124443872ea35bb
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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