Trimethyltin chloride → 5-(2,4-dibenzyloxyphenyl)-2H-tetrazole hydrate

HRID 322852

Reaction equation

HRID 322852 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Sn](Cl)(C)C.[N-:30]=[N+:31]=[N-:32].[Na+]>C1(C)C=CC=CC=1>[OH2:8].[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:10]=1[C:11]1[N:30]=[N:31][NH:32][N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 33557Sodium AzideHCID 103136042,4-Dibenzyloxybenzonitrile

Product 1

HCID 220101945-(2,4-dibenzyloxyphenyl)-2H-tetrazole hydrateYield 137.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2,4-dibenzyloxybenzonitrile (1.89 g) in dry toluene (200 mL) is treated with trimethyltin chloride (6 g) and sodium azide (2 g). The mixture is stirred at reflux for 3 days, evaporated and the residue partitioned between dichloromethane (250 mL) and water (165 mL). The organic phase is washed with brine (165 mL), dried over magnesium sulphate and evaporated. The resulting semi-solid is triturated with ether (30 mL) and the solid washed with pentane and crystallised from a mixture of ethyl acetate and pentane to give 5-(2,4-dibenzyloxyphenyl)-2H-tetrazole hydrate (1.55 g) as a white solid, m.p. 178-179° C. [Elemental analysis:- C,69.7; H,5.02; N,15.4%. Calculated for C21H18N4O2.0.2H2O:- C,68.68; H,5.12; N,15.48%].

Workup

  1. temperatureat reflux for 3 days
  2. customevaporated
  3. customthe residue partitioned between dichloromethane (250 mL) and water (165 mL)
  4. washThe organic phase is washed with brine (165 mL)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe resulting semi-solid is triturated with ether (30 mL)
  8. washthe solid washed with pentane
  9. customcrystallised from a mixture of ethyl acetate and pentane

Sources & evidence

ORD record
ord-d9370944c7b84c908d9d9ac5d14634f6
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Linked notes

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