Methane → HCID 86741873, compound

HRID 247209Notes

Reaction equation

HRID 247209 reaction equation
O=[C:2](Cl)[O:3][C:4](Cl)(Cl)Cl.[NH2:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH2:12][S:13][CH3:14].C>O1CCOCC1>[N-:9]=[C:4]=[O:3].[CH3:2][O:16][C:15](=[O:17])[C@H:10]([CH2:11][CH2:12][S:13][CH3:14])[NH2:9]

Participants

5

Reactant 3

HCID 297MethaneHCID 6137L-MethionineHCID 10426Diphosgene

Product 1

HCID 86741873HCID 86741873, 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 the methyl ester of methionine 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 filtrate is fractionally distilled to give methionine methyl 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 filtrate is fractionally distilled

Sources & evidence

ORD record
ord-bd4e2d89716b402d9576529c7c4bdaa5
Source dataset
uspto-grants-1987_11
Patent number
US04705864

Reaction notes

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