Methane → HCID 22154855, compound

HRID 1111026Notes

Reaction equation

HRID 1111026 reaction equation
[O:1]=[C:2](Cl)OC(Cl)(Cl)Cl.[NH2:9][CH:10]([CH2:15][C:16]([CH3:18])=[CH2:17])[C:11]([O:13][CH3:14])=[O:12].C>O1CCOCC1>[N:9]([CH:10]([CH2:15][C:16]([CH3:18])=[CH2:17])[C:11]([O:13][CH3:14])=[O:12])=[C:2]=[O:1]

Participants

5

Reactant 3

HCID 297MethaneHCID 10426DiphosgeneHCID 10486961HCID 10486961, compound

Product 1

HCID 22154855HCID 22154855, 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 methyl 2-amino-4-methyl-4-pentenoate, prepared as described by D. Ferroud, J. P. Genet, and R. Kiolle in Tetrahedron Letters, 1986, 27, 23-26, 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 methyl 2-isocyanato-4-methyl-4-pentenoate.

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-a61784ef190e4ca3944a19c73a1223fe
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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