3-Nitroaniline → Benzamide, 3-nitro-N-(3-nitrophenyl)-

HRID 65609

Reaction equation

HRID 65609 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)CC)C.[N+:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25])([O-:20])=[O:19]>C(OCC)(=O)C>[N+:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:25])([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 66861Benzamide, 3-nitro-N-(3-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 13.81 g. (0.1 mole) of m-nitroaniline in 100 ml. of dry ethyl acetate is added 11.13 g. (0.11 mole) of triethylamine. To the solution is added a solution of 18.56 g. (0.1 mole) of m-nitrobenzoylchloride in 100 ml of ethyl acetate. The mixture is refluxed for 6.5 hours. The reaction mixture is allowed to stand at room temperature overnight. The precipitate is removed by filtration. The filtrate is evaporated to dryness in vacuo. The residue is recrystallized from absolute ethanol. There is obtained 5.79 g. of yellow needles that melt at 188°-189°.

Workup

  1. additionTo the solution is added a solution of 18.56 g
  2. temperatureThe mixture is refluxed for 6.5 hours
  3. customThe precipitate is removed by filtration
  4. customThe filtrate is evaporated to dryness in vacuo
  5. customThe residue is recrystallized from absolute ethanol
  6. customThere is obtained 5.79 g
  7. customthat melt at 188°-189°

Sources & evidence

ORD record
ord-007f725a2f0c42c8b0ae46b5a365c8aa
Source dataset
uspto-grants-1978_12
Patent number
US04128570

Linked notes

Loading…