Reaction #2069925

Reaction equation

4-Isopropyliodobenzene

N-acetyl-4-isopropylaniline

potassium carbonate

18-crown-6

→

N-Acetyl-N,N-di(4-isopropylphenyl)amine

Solvents

dichloromethane

THF

1,2-dichlorobenzene

Conditions

Workup

1. 1
   Filtrationthe still-hot reaction mixture is filtered
2. 2
   Washthe filter residue is washed thoroughly
3. 3
   Otherthe solvent is removed on a rotary evaporator
4. 4
   OtherThe crude product is chromatographed on silica gel using 10% THF in dichloromethane
5. 5
   ConcentrationThe product fractions are concentrated to dryness
6. 6
   Otherrecrystallized from hexane
7. 7
   Otherdried under reduced pressure

Procedure

4-Isopropyliodobenzene (29.2 g, 118 mmol), N-acetyl-4-isopropylaniline (21.0 g, 118 mmol), copper powder (15.0 g, 237 mmol), potassium carbonate (65.4 g, 474 mmol) and 18-crown-6 (2.9 g, 12 mmol) are heated to reflux in 200 ml of 1,2-dichlorobenzene. The reaction is monitored by thin-layer chromatography (eluent: 10% THF in dichloromethane). After 48 h, the still-hot reaction mixture is filtered, the filter residue is washed thoroughly and the solvent is removed on a rotary evaporator. The crude product is chromatographed on silica gel using 10% THF in dichloromethane. The product fractions are concentrated to dryness, recrystallized from hexane and dried under reduced pressure.

Source