Ammonia → Diethyl (aminomethylidene)propanedioate

HRID 2271101Notes

Reaction equation

HRID 2271101 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH3:16].C(O)C>>[NH2:16][CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 6871Diethyl (ethoxymethylene)malonate

Product 1

HCID 226751Diethyl (aminomethylidene)propanedioate

Procedure

To diethyl ethoxymethylenemalonate (50.13 g, 0.232 mmol), cooled to −20° C. under nitrogen, was added a 2.0 M solution of ammonia in ethanol (232 ml, 0.464 mmol) and the resulting solution was stirred at room temperature overnight. The solution was then evaporated in vacuo to give a quantitative yield of the title compound as a cream solid; 1H NMR (360 MHz, CDCl3) 5 1.28 (3H, t, J 7.1 Hz), 1.35 (3H, t, J 7.1 Hz), 4.19 (2H, q, J 7.1 Hz), 4.26 (2H, q, J 7.1 Hz), 5.68 (1H, br s), 8.11 (1H, dd), 8.69 (1H, br s).

Workup

  1. customThe solution was then evaporated in vacuo

Sources & evidence

ORD record
ord-9224fbd8a51e49bf9c8e887ba0a932a3
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

Loading…