O-Toluidine → N-(2-methylphenyl)-4-methylvaleramide

HRID 431799Notes

Reaction equation

HRID 431799 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][CH:14]([CH3:20])[CH2:15][CH2:16][C:17]([OH:19])=O.[NH2:21][C:22]1[C:23]([CH3:28])=[CH:24][CH:25]=[CH:26][CH:27]=1>ClCCl>[CH3:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:17](=[O:19])[CH2:16][CH2:15][CH:14]([CH3:13])[CH3:20]

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 12587Isocaproic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 22708317N-(2-methylphenyl)-4-methylvaleramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Carbonyldiimidazole (65 g) was mixed with 500 ml of dry dichloromethane in a 2-L round bottom flask and stirred magnetically. A solution of 4-methylvaleric acid in 200 ml of dichloromethane was added dropwise over 45 minutes and the mixture was stirred for another 1.25 hours. o-Toluidine (45 g) in 100 ml of dichloromethane was then added over about 20 minutes. After stirring for 2 hours the mixture was washed with water and then the solvent was stripped on a rotary evaporator. The residue was mixed with 150 ml of methanol and 75 ml of water and put in the freezer. Filtration of the precipitate, dilution of the filtrate with water and refiltration of the precipitate gave 75 g (94%) of vacuum dried N-(2-methylphenyl)-4-methylvaleramide which was used without further treatment in the next step.

Workup

  1. stirringthe mixture was stirred for another 1.25 hours
  2. stirringAfter stirring for 2 hours the mixture
  3. washwas washed with water
  4. customthe solvent was stripped on a rotary evaporator
  5. additionThe residue was mixed with 150 ml of methanol and 75 ml of water
  6. filtrationFiltration of the precipitate, dilution of the filtrate with water and refiltration of the precipitate

Sources & evidence

ORD record
ord-8f017aa8d805437aac87e2831652b7c4
Source dataset
uspto-grants-2003_12
Patent number
US06660763B2

Reaction notes

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