HCID 59359548, compound → HCID 59359513, compound

HRID 383212Notes

Reaction equation

HRID 383212 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]1[C:15]([NH2:20])=[CH:16][CH:17]=[CH:18][CH:19]=1)([CH3:3])[CH3:2]>C(#N)C>[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=1[N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]=[C:1]1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:12])[CH3:11]

Participants

3

Reactant 1

HCID 59359548HCID 59359548, compound

Product 1

HCID 59359513HCID 59359513, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N1-(2,6-diisopropylphenyl)benzene-1,2-diamine (8.5 g, 32 mmol) and benzldehyde (3 g, 28.8 mmol) were reacted in acetonitrile (100 ml) under reflux for 3 hours. The reaction mixture was cooled to room temperature. Ferric chloride (0.05 g, 0.28 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. 3.4 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

Sources & evidence

ORD record
ord-a3a8d3c2613447acba254d6162d7c5c4
Source dataset
uspto-grants-2013_02
Patent number
US08367223B2

Reaction notes

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