Diethyl (ethoxymethylene)malonate → diethyl N-(3-oxo-1-cyclohexen-1-yl)-aminomethylenemalonate

HRID 1680526Notes

Reaction equation

HRID 1680526 reaction equation
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[CH2:9]([O:11][C:12](=[O:23])[C:13](=[CH:19]OCC)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:10]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:9]([O:11][C:12](=[O:23])[C:13](=[CH:19][NH:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:10]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 788923-Aminocyclohex-2-en-1-one

Product 1

HCID 12877078diethyl N-(3-oxo-1-cyclohexen-1-yl)-aminomethylenemalonateYield 70.5%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of 11.1 g of 3-amino-2-cyclohexenone, 24.2 g of ethoxymethylenemalonic acid diethyl ester, and 0.12 g of p-toluenesulfonic acid was heated on an oil bath at 120°-130° C. for 2 hours. Using column chromatography, the reaction product was purified to obtain a yield of 19.8 g of N-(3-oxo-1-cyclohexen-1-yl)aminomethylenemalonic acid diethyl ester in the form of a pale-yellow viscous oil. The n.m.r. spectrum (d6 -DMSO, 60Mc, TMS) of this compound had signals at δ values of 1.24 (3H, t, J=7 Hz), 1.26 (3H, t, J=7 Hz), 1.7-2.75 (6H, m), 4.10 (2H, q, J=7 Hz), 4.18 (2H, q, J=7 Hz), 5.75 (H, s), 8.05 (1H, d, J=13.8 Hz), and 10.2 (1H, d, J=13.8 Hz).

Workup

  1. temperaturewas heated on an oil bath at 120°-130° C. for 2 hours
  2. customthe reaction product was purified

Sources & evidence

ORD record
ord-0c45a560e07f436f9d6cf451093620bf
Source dataset
uspto-grants-1981_06
Patent number
US04273932

Reaction notes

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