Urea → 4-Nitrobenzamide

HRID 1079090Notes

Reaction equation

HRID 1079090 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>ClC1C=CC=CC=1C.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 90.3%

Reagents, catalysts & solvents 2

HCID 107909Phosphorous acidCatalystHCID 72382-ChlorotolueneSolvent

Conditions

Temperature
25 °C

Procedure

83.5 g (0.5 mol) of 4-nitrobenzoic acid, 33.0 g (0.55 mol) of urea and 0.5 g of phosphorous acid are heated in 250 ml of o-chlorotoluene with stirring at from 150° to 157° C. for 8 h. After cooling to 25° C. the solid is filtered off with suction and washed with 50 ml of o-chlorotoluene. The filter cake is introduced into 250 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. 74.9 g of 4-nitrobenzamide are obtained having a melting point of from 194 to 195° C. This corresponds to a yield of 90.3% of theory. By acidification of the aqueous mother liquor to pH 2, 3.4 g of 4-nitrobenzoic acid (4.1% of theory) are obtained which can be employed again in a subsequent batch.

Workup

  1. filtrationis filtered off with suction
  2. washwashed with 50 ml of o-chlorotoluene
  3. additionThe filter cake is introduced into 250 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-126e8703b45645518ed36329a0ca85ca
Source dataset
uspto-grants-1996_08
Patent number
US05550286

Reaction notes

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