Urea → 4-Nitrobenzamide

HRID 1079097Notes

Reaction equation

HRID 1079097 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>C1C(Cl)=CC=C(Cl)C=1.S(=O)(=O)(O)N>[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 48.9%

Reagents, catalysts & solvents 2

HCID 5987Sulfamic AcidCatalystHCID 46851,4-DichlorobenzeneSolvent

Conditions

Temperature
25 °C

Procedure

83.5 g (0.50 mol) of 4-nitrobenzoic acid, 30.0 g (0.50 mol) of urea and 0.5 g of sulfamic acid are heated in 200 ml of dichlorobenzene with stirring at from 180° to 181° C. for 16 h. After cooling to 25° C. the solid is filtered off with suction and is washed with 50 ml of dichlorobenzene. 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. 40.6 g of 4-nitrobenzamide are obtained having a melting point of from 192° to 195° C. This corresponds to a yield of 48.9% of theory.

Workup

  1. filtrationis filtered off with suction
  2. washis washed with 50 ml of dichlorobenzene
  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-4b9fb47ebc6f4106988f27d15fe32513
Source dataset
uspto-grants-1996_08
Patent number
US05550286

Reaction notes

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