Methane → HCID 86742137, compound

HRID 1111015Notes

Reaction equation

HRID 1111015 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[C:9]1([O:15][C:16](=[O:19])[CH2:17][NH2:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C>O1CCOCC1>[N-:18]=[C:4]=[O:3].[C:9]1([O:15][C:16](=[O:19])[CH2:17][NH2:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 10426DiphosgeneHCID 12783661HCID 12783661, compound

Product 1

HCID 86742137HCID 86742137, 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 phenyl 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 phenyl 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-62c957541ce7405884ea9b188f8a1908
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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