Methane → Dimethyl isocyanatomalonate

HRID 1607834Notes

Reaction equation

HRID 1607834 reaction equation
[O:1]=[C:2](Cl)[O:3][C:4](Cl)(Cl)Cl.Cl.[NH2:10][CH:11]([C:15]([OH:17])=[O:16])C(O)=O.[CH4:18].[O:19]1CCOC[CH2:20]1>>[N:10]([CH:11]([C:15]([O:17][CH3:18])=[O:16])[C:2]([O:3][CH3:4])=[O:1])=[C:20]=[O:19]

Participants

5

Reactant 4

HCID 297MethaneHCID 10426DiphosgeneHCID 312751,4-DioxaneHCID 85573820Aminomalonate hydrochloride

Product 1

HCID 14876291Dimethyl isocyanatomalonateYield 80%

Procedure

9.7 mL diphosgene is added dropwise over 50 minutes to a mixture of 12.85 gdiemthyl aminomalonate hydrochloride and 0.1 g activated charcoal in 25 mL dioxane under N2. The reaction mixture warms to 75°-80°C. during this time. 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 moistureto a minimum. The crude product is purified by fractional distillation (bp 80°-85° C., <1 mm Hg) to give pure dimethyl isocyanatomalonate in >80% yield.

Workup

  1. customwarms to 75°-80°C. during this time
  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. distillationThe crude product is purified by fractional distillation (bp 80°-85° C., <1 mm Hg)

Sources & evidence

ORD record
ord-dafe58d188f74fd2b25ecd8ad268ff22
Source dataset
uspto-grants-1989_09
Patent number
US04868061

Reaction notes

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