m-Toluidine → 2-Methyl-N-(m-tolyl)benzamide

HRID 1886973Notes

Reaction equation

HRID 1886973 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.[OH-].[Na+].[CH3:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>CC(C)=O.O>[CH3:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1)=[O:15]

Participants

6

Reactant 3

HCID 7934m-ToluidineHCID 14798Sodium HydroxideHCID 702762-Methylbenzoyl chloride

Product 1

HCID 952902-Methyl-N-(m-tolyl)benzamideYield 96.62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

m-Toluidine (1772 g) is dissolved in acetone (3.5 L), and thereto is added a solution of sodium hydroxide (648 g) in water (6.25 L), and the mixture is cooled to around 20° C. To the mixture is added o-methylbenzoyl chloride (2507 g) over a period of about 20 minutes with stirring, by which the temperature of the reaction mixture raises to around 60° C. After stirring for about one hour, the reaction mixture is cooled around 10° C. and the resulting crystals are taken by filtration. The crystalline product is washed 2 times with methanol/water (4:1, 3.75 L), and dried at about 60° C. to give the desired product (3530 g, yield 96.62%).

Workup

  1. temperatureraises to around 60° C
  2. stirringAfter stirring for about one hour
  3. temperaturethe reaction mixture is cooled around 10° C.
  4. filtrationthe resulting crystals are taken by filtration
  5. washThe crystalline product is washed 2 times with methanol/water (4:1, 3.75 L)
  6. customdried at about 60° C.

Sources & evidence

ORD record
ord-90075a14ebe340a0a8ada65c18ddef9d
Source dataset
uspto-grants-2013_08
Patent number
US08501730B2

Reaction notes

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