Water → 5-Phenyl-2-trityltetrazole

HRID 466821

Reaction equation

HRID 466821 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.C1COCC1>[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 100.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-phenyltetrazole (5 g; 34 mmole), stirring in 55 mL of acetone, was added 3.6 g of triethylamine (36 mmoles). The mixture was aged for 15 minutes after which triphenylmethylchloride (10.0 g; 36 mmoles) in 20 mL of THF was added; the temperature rose 8°-10° C. After stirring for 1 hour, 75 mL of H2O was added and the mixture stirred for 1 hour. After filtration, washing with water and drying in vacuo at 70° C., 13.3 g of 18a was obtained.

Workup

  1. customrose 8°-10° C
  2. stirringthe mixture stirred for 1 hour
  3. filtrationAfter filtration
  4. washwashing with water
  5. customdrying in vacuo at 70° C.

Sources & evidence

ORD record
ord-47d3016f67464ec7b2cbdc3d2cc81882
Source dataset
uspto-grants-1992_10
Patent number
US05157040

Linked notes

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