Carbamic acid, ethyl ester → HCID 13765534, compound

HRID 652577Notes

Reaction equation

HRID 652577 reaction equation
[CH:1](=O)/[CH:2]=[CH:3]/[CH3:4].[C:6](=[O:11])([O:8][CH2:9][CH3:10])[NH2:7]>COC1C=CC(O)=CC=1.ClC=C(Cl)Cl>[CH3:4][CH:3]([NH:7][C:6]([O:8][CH2:9][CH3:10])=[O:11])[CH2:2][CH:1]([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 447466Crotonaldehyde

Product 1

HCID 13765534HCID 13765534, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 6575TrichloroethyleneSolvent

Procedure

35 g of crotonaldehyde are added dropwise at 60°-83° C. to a mixture of 133.5 g of ethyl carbamate, 15 g of acid ion exchanger resin (Duolite C 265), 0.2 g of hydroquinone monomethyl ether and 200 ml of trichloroethylene in the course of 20 minutes, and the mixture is thereafter left at 80° C. for 30 minutes. The catalyst is filtered off, the solvent is distilled off and the residue is crystallized from ethyl acetate/petroleum ether. This gives 83 g (52% yield, based on starting crotonaldehyde) of 3-methyl-1,1,3-tri(ethoxycarbonylamino)propane having a melting point of 103°-105° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. distillationthe solvent is distilled off
  3. customthe residue is crystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-5f897e01cb5243f4ab3d98753db51f7a
Source dataset
uspto-grants-1987_06
Patent number
US04672137

Reaction notes

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