p-Toluenesulfonic acid → HCID 12980024, compound

HRID 1796574Notes

Reaction equation

HRID 1796574 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)[CH2:15][CH3:16].CC1C=CC(S(O)(=O)=O)=CC=1>>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[N:6]=[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH3:16])([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 71481-Phenyl-1-propanoneHCID 32484Diisopropylaniline

Product 1

HCID 12980024HCID 12980024, compoundYield 73.3%

Conditions

Temperature
205 °C

Procedure

2,6-Diisopropylaniline (3.8 mL, 20 mmol, Aldrich) was mixed with propiophenone (2.7 mL, 20 mmol, Aldrich) and p-TsOH (0.4 g, 2.1 mmol, Aldrich). The resulting mixture was heated at 205° C. for 1.5 h under a slow stream of Ar to remove H2O that formed. After cooling to RT the reaction mixture was poured into hexanes (50 mL), filtered, the precipitate was washed with additional hexanes (2×20 mL) followed by the evaporation of the filtrate and distillation of the residue. After the initial fraction of starting materials (80–110° C./0.5 mm) the product was collected as a yellow oil, bp 110–125° C./0.5 mm. Crystallization from methanol at −30° C. it afforded product as yellow crystals (4.3 g, 73.3%). 1H NMR (CDCl3) 7.99–7.91 (m, 2H); 7.54–7.44 (m, 3H); 7.20–7.13 (m, 2H); 7.12–7.04 (m, 1H); 2.78 (septet, 2H; J=6.9 Hz); 2.53 (q, 2H; J=7.7 Hz); 1.21 (d, 6H; J=6.9 Hz); 1.16 (d, 6H; J=6.9 Hz); 0.99 (t, 3H; J=7.7 Hz).

Workup

  1. customto remove H2O
  2. customthat formed
  3. temperatureAfter cooling to RT the reaction mixture
  4. filtrationfiltered
  5. washthe precipitate was washed with additional hexanes (2×20 mL)
  6. customfollowed by the evaporation of the filtrate and distillation of the residue
  7. customAfter the initial fraction of starting materials (80–110° C./0.5 mm) the product was collected as a yellow oil, bp 110–125° C./0.5 mm
  8. customCrystallization from methanol at −30° C. it

Sources & evidence

ORD record
ord-0fedf42134514022aee0594d31257125
Source dataset
uspto-grants-2006_04
Patent number
US07030200B2

Reaction notes

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