p-Toluenesulfonic acid → HCID 178439035, compound

HRID 887988Notes

Reaction equation

HRID 887988 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Br:9])[N:4]=1)=O.[CH:10]([C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([CH3:22])[CH3:21])[C:14]=1[NH2:15])([CH3:12])[CH3:11].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:9][C:5]1[NH:4][C:3](=[N:15][C:14]2[C:16]([CH:20]([CH3:21])[CH3:22])=[CH:17][CH:18]=[CH:19][C:13]=2[CH:10]([CH3:12])[CH3:11])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 32484DiisopropylanilineHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 178439035HCID 178439035, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Prepare a mixture of the 2-formyl-6-bromopyridine (72 g, 0.38 mol) of Step (a) and 2,6-diisopropylaniline (73 g, 0.38 mmol) in 500 mL of anhydrous toluene containing 0.3 nanometer (nm) pore size molecular sieves (6 g) and 80 mg of 4-methylbenzenesulfonic acid (p-TsOH) to give a mixture. Add the mixture to a dry, 500 mL 3-neck round bottom flask equipped with a condenser, an overhead mechanical stirrer, and a thermocouple well. Heat the mixture to 70° C. under a nitrogen gas atmosphere and stir for 12 hours. Cool the mixture to room temperature, filter it, and remove volatiles under reduced pressure until a constant weight to give the 6-bromo-2-(2,6-diisopropylphenyl)iminopyridine as a brown oil. Yield is 0.11 kg (82%). GC/MS 346 (M+), 331, 289, 189, 173, 159, 147, 131, 116, 103, 91, 78. Use the 6-bromo-2-(2,6-diisopropylphenyl)iminopyridine without further purification in step (c) below.

Workup

  1. customPrepare
  2. customto give a mixture
  3. additionAdd the mixture to a dry, 500 mL 3-neck round bottom flask
  4. customequipped with a condenser, an overhead mechanical stirrer
  5. temperatureCool the mixture to room temperature
  6. filtrationfilter it
  7. customremove volatiles under reduced pressure until a constant weight

Sources & evidence

ORD record
ord-e383f8dbdf934472858eefcd87cc5fbf
Source dataset
uspto-grants-2012_08
Patent number
US08247553B2

Reaction notes

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