Trityl chloride → 5-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(triphenylmethyl)-1H-tetrazole

HRID 847104Notes

Reaction equation

HRID 847104 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]#[N:10])=[CH:3][CH:2]=1.[N-:16]=[N+:17]=[N-:18].[Na+].C([Sn](Cl)(CCCC)CCCC)CCC.[OH-].[Na+].[C:36]1([C:42](Cl)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1(C)C=CC=CC=1.CCCCCCC.O>[C:36]1([C:42]([N:10]2[C:9]([C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[C:4]3[CH:5]=[CH:6][C:1]([CH3:15])=[CH:2][CH:3]=3)=[N:18][N:17]=[N:16]2)([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

9

Reactant 5

HCID 6456Trityl chlorideHCID 14798Sodium HydroxideHCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 101520195-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(triphenylmethyl)-1H-tetrazole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8900HeptaneSolvent

Conditions

Temperature
110 °C

Procedure

2-(p-Tolyl)benzonitrile (9.00 g), sodium azide (3.00 g), toluene (35 ml) and tributyltin chloride (16.4 g) were charged to a 250 ml round-bottomed flask equipped with mechanical stirrer, condenser with N2 inlet and thermometer, in a heating mantle. The mixture was heated to 110° C. and held for 70 hours. The mixture was diluted with 35 ml toluene and cooled to room temperature. 10N Sodium hydroxide (5.5 ml) and triphenylmethylchloride (13.5 g) were added and the mixture stirred 3 hours at room temperature. D.I. water (35 ml) and heptane (70 ml) were added and the resulting slurry cooled in an ice bath 11/2 hours. The mixture was vacuum filtered, washed 2×50 ml water and once with 50 ml (3/2, V/V) heptane/toluene, and dried in vacuo overnight at 40° C. Crude Yield=18.32 g, 82.2%. The crude product was dissolved in methylene chloride (200 ml) and washed 1× 52 ml 0.4N sodium hydroxide. The organic phase was gravity filtered, stripped on a rotary evaporator and the product reslurried with heptane (100 ml), filtered and dried in vacuo at 40° C. overnight. Overall Yield: 15.1 g, 68%. M.P.: 161°-162° C.

Workup

  1. customequipped with mechanical stirrer, condenser with N2 inlet
  2. temperaturecooled to room temperature
  3. temperaturethe resulting slurry cooled in an ice bath 11/2 hours
  4. filtrationfiltered
  5. washwashed 2×50 ml water
  6. dry with materialonce with 50 ml (3/2, V/V) heptane/toluene, and dried in vacuo overnight at 40° C
  7. dissolutionThe crude product was dissolved in methylene chloride (200 ml)
  8. washwashed 1× 52 ml 0.4N sodium hydroxide
  9. filtrationfiltered
  10. customstripped on a rotary evaporator
  11. filtrationfiltered
  12. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-6743967314134e9dbcca6a229a56b208
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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