Carbamic acid, ethyl ester → HCID 13765531, compound

HRID 652573Notes

Reaction equation

HRID 652573 reaction equation
O=[CH:2][C:3](=[CH2:5])[CH3:4].[C:6](=[O:11])([O:8][CH2:9][CH3:10])[NH2:7]>COC1C=CC(O)=CC=1.C(Cl)(Cl)Cl>[CH3:4][CH:3]([CH2:2][NH:7][C:6]([O:8][CH2:9][CH3:10])=[O:11])[CH:5]([NH:7][C:6]([O:8][CH2:9][CH3:10])=[O:11])[NH:7][C:6]([O:8][CH2:9][CH3:10])=[O:11]

Participants

5

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 6562Methacrolein

Product 1

HCID 13765531HCID 13765531, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 6212ChloroformSolvent

Procedure

35 g of methacrolein are added dropwise at 60°-65° C. to a mixture of 133.5 g of ethyl carbamate, 30 g of acid ion exchanger resin (Duolite C 265), 0.4 g of hydroquinone monomethyl ether and 400 ml of chloroform in the course of 40 minutes. The mixture is left at that temperature for 1 hour, the ion exchanger is filtered off, the chloroform is distilled off, and the residue is crystallized from ethyl acetate/petroleum ether. This gives 97 g of 2-methyl-1,1,3-tri(ethoxycarbonylamino)propane (60.8% yield, based on starting methacrolein) having a melting point of 138°-140° C.

Workup

  1. filtrationthe ion exchanger is filtered off
  2. distillationthe chloroform is distilled off
  3. customthe residue is crystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-c525e6be7e7b49e8ad067f8a2b7db111
Source dataset
uspto-grants-1987_06
Patent number
US04672137

Reaction notes

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