Urea → 4-Nitrobenzamide

HRID 1079096Notes

Reaction equation

HRID 1079096 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13]C(N)=O>C1(C)C=C(C)C=C(C)C=1.P(=O)(O)(O)O>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 1176UreaHCID 61084-Nitrobenzoic Acid

Product 1

HCID 120914-NitrobenzamideYield 62.7%

Reagents, catalysts & solvents 2

HCID 1004Phosphoric AcidCatalystHCID 7947MesityleneSolvent

Conditions

Temperature
25 °C

Procedure

83.5 g (0.50 mol) of 4-nitrobenzoic acid, 30.0 g (0.50 mol) of urea and 1 g of phosphoric acid are heated in 250 ml of mesitylene with stirring at from 160° to 162° C. for 8 h. After cooling to 25° C. the solid is filtered off with suction and is washed with 25 ml of mesitylene. The filter cake is introduced into 250 ml of water and the mixture is adjusted to a pH of 12 with aqueous sodium hydroxide solution and subjected to steam distillation. Subsequently the solid is filtered off with suction and is dried at 100° C. 52.0 g of 4-nitrobenzamide are obtained having a melting point of from 193° to 195° C. This corresponds to a yield of 62.7% of theory.

Workup

  1. filtrationis filtered off with suction
  2. washis washed with 25 ml of mesitylene
  3. additionThe filter cake is introduced into 250 ml of water
  4. distillationsubjected to steam distillation
  5. filtrationSubsequently the solid is filtered off with suction
  6. customis dried at 100° C

Sources & evidence

ORD record
ord-5a129a33806543cf9e78593d3ff763a2
Source dataset
uspto-grants-1996_08
Patent number
US05550286

Reaction notes

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