Aniline → Formanilide

HRID 1390853Notes

Reaction equation

HRID 1390853 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].[K]>CO>[CH:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]

Participants

4

Reactant 2

HCID 6115AnilineHCID 8673634955883-46-0

Product 1

HCID 7671Formanilide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Into a 1-liter Parr autoclave equipped with an agitator, thermowell, rupture disc and cooling coils are placed 84 g. (0.9 mole) of aniline, 16 g. (0.1 mole) of potassium formanilide and 150 g. of methanol. The autoclave is closed and purged with CO. The temperature is raised to 100° C. with atm. steam and CO is introduced at 28 kg/cm2 pressure. Absorption is rapid and little or no heat of reaction is noted. The reaction is run for 31/2 hours, the autoclave cooled to 15° C. and the excess CO vented. The methanol is removed by distillation, xylene added and resulting xylene solution washed with 10 ml. of conc. hydrochloric acid and 200 ml. of water. The organic layer is separated and analyzed by gas-liquid chromatography. The yield of formanilide expected is approximately 93%.

Workup

  1. customInto a 1-liter Parr autoclave equipped with an agitator
  2. temperaturethermowell, rupture disc and cooling coils
  3. customThe autoclave is closed
  4. custompurged with CO
  5. additionsteam and CO is introduced at 28 kg/cm2 pressure
  6. customAbsorption
  7. temperaturelittle or no heat of reaction
  8. custom2 hours
  9. temperaturethe autoclave cooled to 15° C.
  10. customThe methanol is removed by distillation, xylene
  11. additionadded
  12. customresulting xylene solution
  13. washwashed with 10 ml
  14. customThe organic layer is separated

Sources & evidence

ORD record
ord-6963e4ec0ac247f39f78bdd4c60ac559
Source dataset
uspto-grants-1979_02
Patent number
US04140716

Reaction notes

Loading…