Hydrochloric Acid → Formanilide

HRID 1390854Notes

Reaction equation

HRID 1390854 reaction equation
NC1C=CC=CC=1.[CH:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].[Na].CO.Cl>C1(C)C(C)=CC=CC=1>[CH:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6115AnilineHCID 86736350HCID 86736350, compound2×

Product 1

HCID 7671Formanilide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

To the reactor described in Example 1, there is placed 84 grams (0.9 mole) of aniline, 14 grams (0.1 mole) of sodium formanilide and 150 grams of methanol. The autoclave is closed and purged with carbon monoxide. The temperature of the autoclave is raised to 100° C. with atmospheric steam and carbon monoxide introduced at 28 kg/cm2 pressure for 31/2 hours. The reaction mixture is then cooled and vented, and the methanol removed by distillation. Xylene is added and the xylene solution washed with 0.1 moles hydrochloric acid to hydrolyze the sodium formanilide and the organic layer separated. Analysis shows that the yield of formanilide is about 86%.

Workup

  1. customThe autoclave is closed
  2. custompurged with carbon monoxide
  3. additionintroduced at 28 kg/cm2 pressure for 31/2 hours
  4. temperatureThe reaction mixture is then cooled
  5. customthe methanol removed by distillation
  6. additionXylene is added
  7. customthe organic layer separated

Sources & evidence

ORD record
ord-69040fdfd01b4096b8870d6308b826c0
Source dataset
uspto-grants-1979_02
Patent number
US04140716

Reaction notes

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