Aniline → 2-Toluanilide

HRID 1757376Notes

Reaction equation

HRID 1757376 reaction equation
[Cl-].[Ca+2].[Cl-].[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:11]1([CH3:20])[C:12]([C:17](Cl)=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1>N1C=CC=CC=1>[CH3:20][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:18]

Participants

5

Reactant 3

HCID 6115AnilineHCID 702762-Methylbenzoyl chlorideHCID 5284359Calcium Chloride

Product 1

HCID 234662-Toluanilide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A three necked flack having a capacity of 100 ml, and equipped with a dropping funnel, a thermometer and a drying tube packed with calcium chloride, was charged with 11.2 g of aniline and 30 ml of pyridine. While stirring the solution in the flack by using a magnetic stirrer, 18.5 g of o-toluoyl chloride was added dropwise from the dropping funnel to the solution in such a manner that the temperature of the resultant reaction mixture did not exceed a level of 40° C. Simultaneously with the start of the dropwise addition, an exothermic reaction occurred, and a solid substance was gradually precipitated. Finally, the entire reaction system was solidified so that the stirring became impossible. The reactionwas completed after 2 hours from the start thereof. To the reaction system,an acid water containing hydrochloric acid was added, and then the solid product was pulverized and filtered to collect the reaction product. The reaction product was recrystallized by using a mixed solvent consisting ofethyl alcohol and water. White crystals were obtained in an amount of 24.1 g, and had a melting temperature of 127° C. to 129° C. An NMR measurement, a mass spectrometric analysis and an IR measurement identified that the resultant crystals consisted of the aimed compound.

Workup

  1. customequipped with a dropping funnel
  2. customreaction mixture
  3. customa level of 40° C
  4. additionSimultaneously with the start of the dropwise addition
  5. customan exothermic reaction
  6. customa solid substance was gradually precipitated
  7. additionTo the reaction system,an acid water containing hydrochloric acid
  8. additionwas added
  9. filtrationfiltered
  10. customto collect the reaction product
  11. customThe reaction product was recrystallized
  12. customWhite crystals were obtained in an amount of 24.1 g

Sources & evidence

ORD record
ord-ee9b6dd523cf48e89cd12f76b7b7e86d
Source dataset
uspto-grants-1995_08
Patent number
US05446010

Reaction notes

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