Acetic Anhydride → N-(3-Methylphenyl)acetamide

HRID 846497Notes

Reaction equation

HRID 846497 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1>O>[C:5]([NH:8][C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 7934m-Toluidine

Product 1

HCID 10843N-(3-Methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic anhydride (176 mL) was added slowly to a stirred mixture of 103.2 mL of m-toluidine in 300 mL of water. After complete addition, the mixture was stirred for 4 hours at room temperature. The mixture was cooled in an ice bath, then extracted with diethyl ether. The ether extract was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave an oily residue which solidified. The solid was collected, washed with water, then dissolved in diethyl ether. The etheral solution was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under reduced pressure to yield 3-acetamidotoluene as a solid, mp 59°-61° C.

Workup

  1. additionAfter complete addition
  2. temperatureThe mixture was cooled in an ice bath
  3. extractionextracted with diethyl ether
  4. extractionThe ether extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure
  8. customto leave an oily residue which
  9. customThe solid was collected
  10. washwashed with water
  11. dissolutiondissolved in diethyl ether
  12. dry with materialThe etheral solution was dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-ba1fef963b524c1eb0fe0df687d44098
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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