Toluene → Valeranilide

HRID 1977655Notes

Reaction equation

HRID 1977655 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C([C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13])CC.[C:18]1(C)[CH:23]=CC=C[CH:19]=1>>[CH2:19]([CH2:6][C:5]([NH:13][C:12]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:11]=1)=[O:7])[CH2:18][CH3:23]

Participants

4

Reactant 3

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 157592-Propylaniline

Product 1

HCID 82501ValeranilideYield 96%

Procedure

Acetic anhydride (7.5 ml) was added to a toluene (100 ml) solution of 2-propylaniline, and the mixture was stirred at room temperature for 2 hours. Crystals thus precipitated were collected by filtration and washed with hexane. The filtrate was concentrated under reduced pressure. After hexane was added thereto, tritulation was conducted. The deposited crystals were collected by filtration and washed with hexane. By the above crystallization steps, 2-propylacetanilide (13.0 g; yield, 96%) was obtained as white crystals.

Workup

  1. customCrystals thus precipitated
  2. filtrationwere collected by filtration
  3. washwashed with hexane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionAfter hexane was added
  6. filtrationThe deposited crystals were collected by filtration
  7. washwashed with hexane
  8. customBy the above crystallization steps

Sources & evidence

ORD record
ord-4496c910cfc64e359c0b551655c16026
Source dataset
uspto-grants-2001_05
Patent number
US06235730B1

Reaction notes

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