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

HRID 653940Notes

Reaction equation

HRID 653940 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.C(Cl)Cl.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

10

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 4

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 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. 10 N 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 0.4 N 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. customCrude Yield =18.32 g, 82.2%
  8. washwashed 1×52 ml 0.4 N 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-5efb7b6eacf64fc48953ab7453c92a4e
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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