Water → 5-Phenyl-2-trityltetrazole

HRID 1591424Notes

Reaction equation

HRID 1591424 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.C(N(CC)CC)C.[C:19]1([C:25](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CC(C)=O.O1CCCC1>[C:1]1([C:7]2[N:8]=[N:9][N:10]([C:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418369HCID 178418369, compound

Product 1

HCID 32929595-Phenyl-2-trityltetrazoleYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5.0 g (34.2 mmol) of 5-phenyltetrazole in 55 mL of acetone was added 5.0 mL of triethylamine (3.6 g, 35.6 mmol, 1.04 eq). After 15 minutes, a solution of 10.0 g of triphenylmethyl chloride (35.9 mmol, 1.05 eq) in 20 mL of tetrahydrofuran was added and the mixture stirred at room temperature for one hour. Water (75 mL) was slowly added and the mixture stirred for one hour at room temperature. The product was collected by filtration, washed with 75 mL of water and dried at 60° C. under vacuum to give 13.3 g (34.2 mmol, 100%) of the product.

Workup

  1. stirringthe mixture stirred for one hour at room temperature
  2. filtrationThe product was collected by filtration
  3. washwashed with 75 mL of water
  4. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-4c0f756bef944beb95f91ccc2812e7f4
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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