2-Cyano-4'-methylbiphenyl → L-158507

HRID 375458Notes

Reaction equation

HRID 375458 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])=[CH:4][CH:3]=1.C([Sn]([N:53]=[N+:54]=[N-:55])(CCCCCCCCCCCC)CCCCCCCCCCCC)CCCCCCCCCCC>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:10]3[N:55]=[N:54][NH:53][N:11]=3)=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1455122-Cyano-4'-methylbiphenylHCID 131719250HCID 131719250, compound

Product 1

HCID 9794697L-158507Yield 82.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.50 g of 2-(4-methylphenyl)benzonitrile, 19.5 g of tridodecyltin azide (tri-n-dodecyltin azide) and 7 ml of toluene was stirred for 37.5 hours at 120° C. The reaction mixture was, after cooling, concentrated, and there were added 18 ml of ethanol, 1 ml of methylene chloride and 2.4 g of sodium nitrite dissolved in 9 ml of water, whose pH was adjusted at 3.4 with conc. hydrochloric acid. To the mixture were added 2 ml of ethyl acetate and 100 ml of hexane. Insolubles were filtered off. The filtrate was shaken, then left standing to form two layers. The organic layer was subjected to extraction with 1N NaOH. The alkaline layer was adjusted at pH 3 with conc. hydrochloric acid, and then subjected to extraction with ethyl acetate. The extract was concentrated, and there were added ethyl acetate and hexane to cause crystallization. The crystals were collected by filtration, washed with hexane and dried to afford 1.51 g (yield 82.3%) of 5-[2-(4'-methylbiphenyl)]tetrazole. Spectrum data were in good agreement with those in Example 4.

Workup

  1. temperatureafter cooling
  2. concentrationconcentrated
  3. additionthere were added 18 ml of ethanol, 1 ml of methylene chloride and 2.4 g of sodium nitrite
  4. dissolutiondissolved in 9 ml of water
  5. additionTo the mixture were added 2 ml of ethyl acetate and 100 ml of hexane
  6. filtrationInsolubles were filtered off
  7. stirringThe filtrate was shaken
  8. waitleft
  9. customto form two layers
  10. extractionThe organic layer was subjected to extraction with 1N NaOH
  11. extractionsubjected to extraction with ethyl acetate
  12. concentrationThe extract was concentrated
  13. additionthere were added ethyl acetate and hexane
  14. customcrystallization
  15. filtrationThe crystals were collected by filtration
  16. washwashed with hexane
  17. customdried

Sources & evidence

ORD record
ord-92dea276e9044ca9a28a022b7041b971
Source dataset
uspto-grants-1996_01
Patent number
US05484955

Reaction notes

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