Trityl chloride → 5-phenyl-1-trityl-1H-tetrazole

HRID 1739503Notes

Reaction equation

HRID 1739503 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl.CC(C)=O>[C:1]1([C:7]2[N:11]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:10]=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418369HCID 178418369, compound

Product 1

HCID 104303585-phenyl-1-trityl-1H-tetrazoleYield 89%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-phenyl-1H-tetrazole (21.9 g) and chlorotriphenylmethane (46 g) in methylene chloride (500 ml) was added triethylamine (16.7 g). The resulting mixture was stirred at room temperature for one hour. The reaction mixture was washed successively with water, 10% aqueous citric acid solution and water and was then dried over anhydrous magnesium sulfate, followed by removal through distillation. The residue so obtained was dispersed in acetone, collected by filtration and then dried, whereby 51.8 g of the title compound was obtained.

Workup

  1. washThe reaction mixture was washed successively with water, 10% aqueous citric acid solution and water
  2. dry with materialwas then dried over anhydrous magnesium sulfate
  3. customfollowed by removal through distillation
  4. customThe residue so obtained
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-d05b131efe36448ea3b139a0cdd59790
Source dataset
uspto-grants-1999_10
Patent number
US05965738

Reaction notes

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