p-Toluenesulfonic acid → HCID 85865016, compound

HRID 1796576Notes

Reaction equation

HRID 1796576 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)[CH2:12][CH3:13].CC1C=CC(S(O)(=O)=O)=CC=1>>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[N:6]=[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][CH3:13])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 71481-Phenyl-1-propanoneHCID 125612-Isopropylaniline

Product 1

HCID 85865016HCID 85865016, compound

Conditions

Temperature
200 °C

Procedure

2-Isopropylaniline (11.6 mL, 82 mmol, Aldrich) was mixed with propiophenone (10 mL, 74.5 mmol, Aldrich) and p-TsOH (1.4 g, 7.3 mmol, Aldrich). The resulting mixture was heated for 2 h at 200° C. under a slow stream of Ar to remove H2O that formed. After cooling to RT the reaction mixture was poured into hexanes (100 mL), filtered, the precipitate washed with additional hexanes (2×100 mL) followed by the evaporation of the filtrate. The residue was filtered through a 9×4.1 cm plug of silica gel in hexanes/ether 10/1 (300 mL collected). After evaporation of the solvent the residue was distilled in vacuo. The initial fraction contained unreacted starting materials (45–50 C/0.4 mm), in the next fraction the product was collected as an orange oil, bp 125–135 C/0.4 mm, 8.0 g, (42.7%). 1H NMR (CDCl3) 8.03–7.95 (m, 2H); 7.53–7.46 (m, 3H); 7.34 (dd, 1H; J=1.4; 7.6 Hz); 7.21 (dt, 1H; J=1.4; 7.6 Hz); 7.1 (dt, 1H; J=1.4; 7.6 Hz); 6.65 (dd, 1H; J=1.4; 7.6 Hz); 3.00 (septet, 1 H; J=6.9 Hz); 2.67 (q, 2H; J=7.6 Hz); 1.22 (d, 6H; J=6.8 Hz); 1.11 (t, 3 H; J=7.6 Hz).

Workup

  1. customto remove H2O
  2. customthat formed
  3. temperatureAfter cooling to RT the reaction mixture
  4. filtrationfiltered
  5. washthe precipitate washed with additional hexanes (2×100 mL)
  6. customfollowed by the evaporation of the filtrate
  7. filtrationThe residue was filtered through a 9×4.1 cm plug of silica gel in hexanes/ether 10/1 (300 mL collected)
  8. customAfter evaporation of the solvent the residue
  9. distillationwas distilled in vacuo
  10. customin the next fraction the product was collected as an orange oil, bp 125–135 C/0.4 mm, 8.0 g, (42.7%)

Sources & evidence

ORD record
ord-5b72ae1e32564c4396529950811554be
Source dataset
uspto-grants-2006_04
Patent number
US07030200B2

Reaction notes

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