(1,1'-Biphenyl)-4-carbonitrile → Tris-biphenyl triazine

HRID 1976263Notes

Reaction equation

HRID 1976263 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7](Cl)=O)=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[C:24]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1.[Cl-].[NH4+:39]>ClC1C=CC=CC=1Cl>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:31]=[C:30]([C:27]3[CH:28]=[CH:29][C:24]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:25][CH:26]=3)[N:39]=[C:30]([C:27]3[CH:26]=[CH:25][C:24]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:29][CH:28]=3)[N:31]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 18021(1,1'-Biphenyl)-4-carbonitrileHCID 24386Thionyl ChlorideHCID 25517Ammonium ChlorideHCID 841514-Phenylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11628027Tris-biphenyl triazineYield 72.6%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

In a 100 milliliter round bottom flask there was added 4-biphenylcarbonyl chloride (2.167 grams), 1,2-dichlorobenzene (27.0 milliliters), thionyl chloride (1.0 milliliter), and aluminum chloride (1.33 grams). With stirring, 4-biphenylcarbonitrile (3.58 grams) was added slowly, and the resulting reaction mixture was heated under argon to about 150° C. for 0.5 hour. The temperature of the reaction mixture was reduced to 120° C., then ammonium chloride (1.07 grams) was added in one portion. The reaction mixture was stirred at 150° C. for an additional 20 hours. The reaction flask was removed from the heater and cooled to room temperature, about 25° C. throughout. The resulting mixture was poured into 100 milliliters of methanol and stirred for 20 minutes. The precipitates were collected by filtration and dried in a vacuum oven to afford 3.9 grams of crude product which was further purified by sublimation. The above titled triazinyl product 2,4,6-tris-(4-biphenylyl)-1,3,5-triazine possessed a melting point of 283° C.

Workup

  1. customthe resulting reaction mixture
  2. customwas reduced to 120° C.
  3. stirringThe reaction mixture was stirred at 150° C. for an additional 20 hours
  4. customThe reaction flask was removed from the heater
  5. temperaturecooled to room temperature, about 25° C. throughout
  6. additionThe resulting mixture was poured into 100 milliliters of methanol
  7. stirringstirred for 20 minutes
  8. filtrationThe precipitates were collected by filtration
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d9d7a2706635466bae929f2cd70a3c13
Source dataset
uspto-grants-2001_05
Patent number
US06225467B1

Reaction notes

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