2,4,6-Trimethylaniline → HCID 12980025, compound

HRID 1797233Notes

Reaction equation

HRID 1797233 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]>>[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

3

Reactant 2

HCID 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 TSOH (1.4 g, 7.3 mmol, Aldrich). The resulting mixture was heated for 2 h at 200° C. under a weak stream of Ar to remove formed H2O. After cooling to RT the reaction mixture was poured into hexanes (100 mL), filtered, and 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./53 Pa). The residue was crystallized from methanol at −30° C. 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). 13C NMR (CDCl3): 170.8, 146.4, 138.2, 131.9, 130.3, 128.7, 128.6, 127.7, 125.6, 23.9, 20.9, 18.2, 11.6. Anal. Calcd for C18H21N: C, 86.00; H, 8.42; N, 5.57. Found: C, 85.79; H, 8.41; N, 5.56.

Workup

  1. customto remove
  2. customformed H2O
  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./53 Pa)
  10. customThe residue was crystallized from methanol at −30° C
  11. customProduct was isolated as large orange-yellow crystals, 4.8 g, (25.6%)

Sources & evidence

ORD record
ord-26fc0ec7f9af4c9c9f3ea04e4219a5c8
Source dataset
uspto-grants-2006_04
Patent number
US07034093B2

Reaction notes

Loading…