HCID 29066826, compound → HCID 59359498, compound

HRID 383208Notes

Reaction equation

HRID 383208 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[C:12]([NH2:17])=[CH:13][CH:14]=[CH:15][CH:16]=1)([CH3:3])[CH3:2]>C(#N)C>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]=[C:1]1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 29066826HCID 29066826, compound

Product 1

HCID 59359498HCID 59359498, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N1-(2-isopropylphenyl)benzene-1,2-diamine (20 g, 88 mmol) and benzldehyde (8.5 g, 80 mmol) were reacted in acetonitrile (100 mL) under reflux for 3 hours. The reaction mixture was cooled to room temperature. Ferric chloride (0.13 g, 0.8 mmol) was added. The reaction mixture was heated up again to reflux overnight. Air was bubbled through the reaction while reflux. The solvent was evaporated. The residue was dissolved in dichloromethane (200 mL) and ran through a short silica gel plug. The crude product was purified by column chromatography using dichloromethane to 3% of ethyl acetate in dichloromethane. The product was further purified by recrystallizing form ethanol. 8 g of desired product was obtained.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureThe reaction mixture was heated up again
  3. temperatureto reflux overnight
  4. customAir was bubbled through the reaction
  5. temperaturewhile reflux
  6. customThe solvent was evaporated
  7. dissolutionThe residue was dissolved in dichloromethane (200 mL)
  8. customThe crude product was purified by column chromatography
  9. customThe product was further purified
  10. customby recrystallizing form ethanol

Sources & evidence

ORD record
ord-9dfd000e115247279c86c9bc98e504a1
Source dataset
uspto-grants-2013_02
Patent number
US08367223B2

Reaction notes

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