Methane → HCID 86742132, compound

HRID 1111006Notes

Reaction equation

HRID 1111006 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[CH2:9]([O:12][C:13](=[O:16])[CH2:14][NH2:15])[CH2:10][CH3:11].C>O1CCOCC1>[N-:15]=[C:4]=[O:3].[CH2:9]([O:12][C:13](=[O:16])[CH2:14][NH2:15])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 297MethaneHCID 10426DiphosgeneHCID 2759255Propyl glycinate

Product 1

HCID 86742132HCID 86742132, 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 glycine n-propyl ester 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 glycine n-propyl ester isocyanate.

Workup

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

Sources & evidence

ORD record
ord-3578f660d5dd4a458fc6178ce1fae22e
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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