Diethyl Malonate → 1,3-Di-(4-Nitrophenyl)-2,4,6-(1H,3H,5H)-Pyrimidinetrione

HRID 986692

Reaction equation

HRID 986692 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:23](OCC)(=[O:30])[CH2:24][C:25](OCC)=[O:26].[OH-].[Na+]>C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:25](=[O:26])[CH2:24][C:23](=[O:30])[N:13]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[C:11]2=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 95094,4'-DinitrocarbanilideHCID 14798Sodium Hydroxide

Product 1

HCID 122885271,3-Di-(4-Nitrophenyl)-2,4,6-(1H,3H,5H)-Pyrimidinetrione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,3-Di-(4-nitrophenyl)urea (1.8 g, 0.006 mole), diethyl malonate (1 ml, 0.006 mole), and sodium hydroxide (0.24 g, 0.006 mole) were refluxed in ethanol (100 ml) for three hours. 1,3-Di-(4-nitrophenyl)-2,4,6-(1H,3H,5H)-pyrimidinetrione precipitated as a yellow powder, m.p. greater than 250° C.

Workup

  1. custom1,3-Di-(4-nitrophenyl)-2,4,6-(1H,3H,5H)-pyrimidinetrione precipitated as a yellow powder, m.p. greater than 250° C.

Sources & evidence

ORD record
ord-19e96a362a354a909ca7eb54f7d632bc
Source dataset
uspto-grants-1987_12
Patent number
US04714838

Linked notes

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