Water → 4-methyl-N-(4-methylphenyl)benzamide

HRID 2379904Notes

Reaction equation

HRID 2379904 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=C=O)=[CH:14][CH:13]=1.O>[O-]CC.[Na+].CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7470P-Toluic Acid2×HCID 693254-Methylphenyl isocyanate

Product 1

HCID 5223204-methyl-N-(4-methylphenyl)benzamide

Reagents, catalysts & solvents 2

HCID 2723922Sodium ethoxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

p-Methylbenzoic acid (95.31 grams, 0.70 mole), sodium ethoxide catalyst (0.2144 gram, 0.225% wt. of the p-methylbenzoic acid used) and N,N'-dimethylacetamide (575 grams) are added to a reactor equipped with a reflux condenser and stirred under a nitrogen atmosphere at 35° C. to provide a solution. p-Methylphenyl isocyanate (97.87 grams, 0.735 mole) is added over a two minute period inducing an exotherm to 40° C. At this time, heating of the reactor commences and a 160° C. temperature is achieved 52 minutes later. After three hours at the 160° C. reaction temperature, the reactor is cooled to 30° C. the the contents poured into deionized water (3.50 liters). A precipitated white crystalline product is recovered by filtration of the aqueous slurry then dried in a vacuum oven at 80° C. and 5 mm Hg for fifteen hours. The dry product and methanol (700 milliliters) are stirred together with heating to provide a solution at 63° C. After cooling the methanol solution to 4° C. for fourteen hours, a white crystalline product is filtered off and dried at 70° C. and 5 mm Hg in a vacuum oven to a constant weight of 135.6 grams. Fourier transform infrared spectrophotometric analysis of a potassium chloride pellet of the product confirms the product structure of 4,4'-dimethylbenzanilide (amide carbonyl absorbance at 1649 cm-1 and amide N--H stretching absorbance at 3349 and 3290 (shoulder) cm-1.

Workup

  1. additionare added to a reactor
  2. customequipped with a reflux condenser
  3. customto provide a solution
  4. customto 40° C
  5. temperatureAt this time, heating of the reactor commences and a 160° C. temperature
  6. customAfter three hours at the 160° C. reaction temperature
  7. temperaturethe reactor is cooled to 30° C. the the contents
  8. filtrationA precipitated white crystalline product is recovered by filtration of the aqueous slurry
  9. customthen dried in a vacuum oven at 80° C.
  10. wait5 mm Hg for fifteen hours
  11. stirringThe dry product and methanol (700 milliliters) are stirred together
  12. temperaturewith heating
  13. customto provide a solution at 63° C
  14. filtrationa white crystalline product is filtered off
  15. customdried at 70° C.

Sources & evidence

ORD record
ord-dd2f0cd4dfa9433da19ac35e2875cc5a
Source dataset
uspto-grants-1994_11
Patent number
US05364912

Reaction notes

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