p-Toluenesulfonic acid → HCID 12980025, compound

HRID 1796577Notes

Reaction equation

HRID 1796577 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].[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>>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[N:4]=[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][CH3:13]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 69132,4,6-TrimethylanilineHCID 71481-Phenyl-1-propanone

Product 1

HCID 12980025HCID 12980025, compound

Conditions

Temperature
200 °C

Procedure

2,4,6-Trimethylaniline (11.5 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 which 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 unreacted starting materials were distilled off under vacuum (45–50° C./0.4 mm). The residue was crystallized from methanol. Product was isolated as large orange-yellow crystals, 4.8 g, (25.6%). 1H NMR (CDCl3) 8.00–7.94 (m, 2H); 7.51–7.45 (m, 3H); 6.89 (s, 2H); 2.50 (q, 2H; J=7.7 Hz); 2.31 (s, 3H); 2.04 (s, 6H); 0.98 (t, 3H; J=7.7 Hz).

Workup

  1. customto remove H2O which
  2. customformed
  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 unreacted starting materials
  9. distillationwere distilled off under vacuum (45–50° C./0.4 mm)
  10. customThe residue was crystallized from methanol
  11. customProduct was isolated as large orange-yellow crystals, 4.8 g, (25.6%)

Sources & evidence

ORD record
ord-e45a8a4000d94757a7163684548f6ad5
Source dataset
uspto-grants-2006_04
Patent number
US07030200B2

Reaction notes

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