4-Nitroaniline → 1-Methacryloyl-3-(4-nitrophenyl)urea

HRID 327749Notes

Reaction equation

HRID 327749 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]([N:16]=[C:17]=[O:18])(=[O:15])[C:12]([CH3:14])=[CH2:13]>C(OCC)C>[C:11]([NH:16][C:17]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:18])(=[O:15])[C:12]([CH3:14])=[CH2:13]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 10942374Methacryloyl isocyanate

Product 1

HCID 197335681-Methacryloyl-3-(4-nitrophenyl)ureaYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Into 500 ml of a diethyl ether solution of 13.8 g (0.1 mol) of p-nitroaniline was added dropwise 50 ml of a diethyl ether solution of 11.1 g (0.1 mol) of methacryloyl isocyanate over about 30 minutes in an ice bath. After completion of the addition, the produced crystal was filtered and the filtrate was distilled under a reduced pressure. The yellow solid gathered from the filtration and the distillation residue was recrystallized with methyl ethyl ketone to obtain 19.7 g of 1-methacryloyl-3-(4-nitrophenyl)urea (Compound 1) which had a decomposing point of 241° to 244° C. and was yellow needle crystal.

Workup

  1. additionAfter completion of the addition
  2. filtrationthe produced crystal was filtered
  3. distillationthe filtrate was distilled under a reduced pressure
  4. filtrationThe yellow solid gathered from the filtration
  5. customthe distillation residue was recrystallized with methyl ethyl ketone

Sources & evidence

ORD record
ord-0f5fee034f3846f5bbb1310f62e4ee96
Source dataset
uspto-grants-1993_12
Patent number
US05274061

Reaction notes

Loading…