Benzonitrile → Kyaphenine

HRID 1579975

Reaction equation

HRID 1579975 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O>C(O)C>[C:2]1([C:1]2[N:8]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:8]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:8]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7505BenzonitrileHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 10305KyaphenineYield 66.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

Benzonitrile (5.2 g, 0.05 mol) was added dropwise over a period of 100 sec to 20 ml (34 g, 0.23 mol) of stirred trifluoromethanesulfonic acid with the temperature being allowed to rise as high as 91°C. When the reaction mixture cooled to 25°C, the yellow solution was poured into 100 ml cold ethanol. The yellow color disappeared and a white flocculent precipitate formed. Recrystallization of this precipitate from 150 ml chloroform afforded 3.43 g (66 percent yield) of 2,4,6-triphenyl-s-triazine (white crystals, m.p. 235°-237°C) (Lit. m.p. 232°C, J. Chem. Soc., 1941, 278). The 3.43 g sample of product exhibited no nitrile bands in the infrared spectrum but the infrared spectral band characteristic of the triazine structure was very strong at 6.6μ.

Workup

  1. customto rise as high as 91°C
  2. customa white flocculent precipitate formed
  3. customRecrystallization of this precipitate from 150 ml chloroform

Sources & evidence

ORD record
ord-9db5099ed00f45cd9236e5785e2574f7
Source dataset
uspto-grants-1976_01
Patent number
US03932402

Linked notes

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