Triethylamine → Ethoxycarbonylpropyleneurea

HRID 1770292Notes

Reaction equation

HRID 1770292 reaction equation
[CH2:1]1[CH2:7][NH:6][C:4](=[O:5])[NH:3]C1.[CH2:8]([O:10][C:11](Cl)=[O:12])[CH3:9].[CH2:14](N(CC)CC)C>ClC(Cl)C>[CH2:8]([O:10][C:11]([CH2:14][CH:7]([NH:6][C:4]([NH2:3])=[O:5])[CH3:1])=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 746152(1H)-Pyrimidinone, tetrahydro-

Product 1

HCID 86748426Ethoxycarbonylpropyleneurea

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

Propyleneurea of 30.0 g (0.3 mol), ethylchloroformate of 10.9 g (0.1 mol) and dichloroethane of 100 g were charged in a reaction vessel and refluxed at 85° to 88° C. A solution of triethylamine of 10.1 g (0.1 mol) in dichloroethane of 250 g was added drop by drop to the refluxed mixture in 2.5 hours followed by continuing for further 2 hours. The resulting solution was condensated and a crude product was refined by the column chromatography to obtain ethoxycarbonylpropyleneurea of 2.2 g (12.7%).

Workup

  1. temperaturerefluxed at 85° to 88° C

Sources & evidence

ORD record
ord-796d3e7ba8d14151ad0541a2f5f9e6d6
Source dataset
uspto-grants-1995_01
Patent number
US05385985

Reaction notes

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