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

HRID 248620Notes

Reaction equation

HRID 248620 reaction equation
C[Sn](C)(C)[N:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[N:6][N:5]=[N:4]1.[C:23]1([C:29](Cl)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[C:23]1([C:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:3]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)=[N:6][N:5]=[N:4]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 14425662HCID 14425662, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of N-trimethylstannyl 5 (4'-methylbiphenyl-2-yl)tetrazole (Example 10, 0.4 g) and anhydrous pyridine (10 mL) was treated with triphenylmethyl chloride (0.3 g) and stirred at room temperature under a nitrogen atmosphere for 48 hours. The resulting solution was evaporated and the residue was partitioned between dichloromethane and saturated aqueous CuSO4. The organic layer was dried over MgSO4 and evaporated. The residual solid was triturated with diisopropyl ether and collected by filtration to give the title compound, mp 163°-165° C. (decomp., gas evol.).

Workup

  1. customThe resulting solution was evaporated
  2. customthe residue was partitioned between dichloromethane and saturated aqueous CuSO4
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. customThe residual solid was triturated with diisopropyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-42f3755d37e447c3bfeee3bf5b4c5f88
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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