Chloroform → Valeranilide

HRID 1977668Notes

Reaction equation

HRID 1977668 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N([CH2:10][CH3:11])CC)C.C([C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH2:17])CC.[CH:22](Cl)(Cl)Cl>>[CH2:22]([CH2:2][C:1]([NH:17][C:16]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:15]=1)=[O:3])[CH2:10][CH3:11]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 157592-Propylaniline

Product 1

HCID 82501ValeranilideYield 86%

Procedure

Acetyl chloride (5.6 ml) and triethylamine (12.5 ml) were added dropwise to a chloroform (50 ml) solution of 2-propylaniline (10.5 g) in this order under ice-cooling. The reaction solution was stirred at room temperature for 3 hours. The solution was concentrated under reduced pressure, and the thus-obtained solid was washed with water and collected by filtration. The resulting residue was recrystallized from ethanol-water to obtain 2-propylacetanilide (11.85 g; yield, 86%) as white crystals.

Workup

  1. temperaturecooling
  2. concentrationThe solution was concentrated under reduced pressure
  3. washthe thus-obtained solid was washed with water
  4. filtrationcollected by filtration
  5. customThe resulting residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-956e84a545aa4f52a4101806a621f41d
Source dataset
uspto-grants-2001_05
Patent number
US06235730B1

Reaction notes

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