Silicon tetrachloride → 5-((4-bromophenyl)methyl)-1H-1,2,3,4-tetrazole

HRID 746760Notes

Reaction equation

HRID 746760 reaction equation
[Si](Cl)(Cl)(Cl)Cl.[N-:6]=[N+:7]=[N-:8].[Na+].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([NH2:20])=O)=[CH:13][CH:12]=1>C(#N)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[N:6]=[N:7][NH:8][N:20]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 2569512-(4-Bromophenyl)acetamide

Product 1

HCID 148887005-((4-bromophenyl)methyl)-1H-1,2,3,4-tetrazoleYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

Stir a mixture of SiCl4 (1.7 g, 10 mmol, 2 eq.) and NaN3 (1.95 g, 30 mmol, 6 eq.) in 50 mL of acetonitrile for 2 hours. Add 1.07 g of 2-(4-bromophenyl) acetamide (5 mmol, 1 eq.) and heat to 85° C. for 5 hour. Cool to room temperature and filter off the solid wash the solid with EtOAc. Wash the ester layer with water, saturated aq. sodium chloride, dry over MgSO4 and evaporate the solvent to afford 900 mg title compound (80%). MS (m/e): 237.0.

Workup

  1. temperatureCool to room temperature
  2. filtrationfilter off the solid
  3. washwash the solid with EtOAc
  4. washWash the ester layer with water, saturated aq. sodium chloride
  5. dry with materialdry over MgSO4
  6. customevaporate the solvent

Sources & evidence

ORD record
ord-c7fa27ebe7604930866869907fb0cd87
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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