Urea → 4-Nitrobenzamide

HRID 1079092Notes

Reaction equation

HRID 1079092 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>[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 90.7%

Reagents, catalysts & solvents 2

HCID 107909Phosphorous acidCatalystHCID 7947MesityleneSolvent

Conditions

Temperature
25 °C

Procedure

334 g (2.0 mol) of 4-nitrobenzoic acid, 120 g (2.0 mol) of urea and 2.0 g of phosphorous acid are heated in 1000 ml of mesitylene with stirring at from 158° C. to 163° C. for 8 h. After cooling to 25° C. the solid is filtered off with suction and washed with 200 ml of mesitylene. The filter cake is introduced into 1000 ml of water, the mixture is adjusted to a pH of 12 using aqueous sodium hydroxide solution, and is subjected to steam distillation. Subsequently the solid is filtered off with suction and dried at 100° C. 301.2 g of 4-nitrobenzamide are obtained, having a melting point of from 191° to 194° C. This corresponds to a yield of 90.7% of theory. By acidification of the aqueous mother liquor to pH 2, 12.5 g of 4-nitrobenzoic acid (3.7% of theory) are obtained which can be employed again in a subsequent batch.

Workup

  1. filtrationis filtered off with suction
  2. washwashed with 200 ml of mesitylene
  3. additionThe filter cake is introduced into 1000 ml of water
  4. distillationis subjected to steam distillation
  5. filtrationSubsequently the solid is filtered off with suction
  6. customdried at 100° C

Sources & evidence

ORD record
ord-7ef263da7bac4a2ea3aa56b30729898e
Source dataset
uspto-grants-1996_08
Patent number
US05550286

Reaction notes

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