Benzene → HCID 20222923, compound

HRID 979927Notes

Reaction equation

HRID 979927 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[NH:6][N:5]=[N:4]1)[CH3:2].[Br:9][CH2:10][CH2:11]Br.C1C=CC=CC=1>C(=O)([O-])[O-].[Ag+2].O>[Br:9][CH2:10][CH2:11][O:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[N:5][N:6]=1

Participants

6

Reactant 3

HCID 241BenzeneHCID 78391,2-DibromoethaneHCID 1354729431-ethyl-1,2-dihydro-5H-tetrazol-5-one

Product 1

HCID 20222923HCID 20222923, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 57 parts of 1-ethyl-1,4-dihydro-5H-tetrazol-5one, 69 parts of 1,2-dibromoethane, 564 parts of silver carbonate and 900 parts of benzene was stirred and refluxed over weekend using a water separator (in the darkness). The whole was filtered off over Hyflo while hot, washed with trichloromethane and the filtrate was evaporated to dry. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The second fraction was collected and the eluent was evaporated, yielding 22.3 parts (40%) of 5-(2-bromoethoxy)-1-ethyl-1H-tetrazole (200).

Workup

  1. temperaturerefluxed over weekend
  2. filtrationThe whole was filtered off over Hyflo while hot,
  3. washwashed with trichloromethane
  4. customthe filtrate was evaporated
  5. customto dry
  6. customThe residue was purified by column chromatography over silica gel
  7. customThe second fraction was collected
  8. customthe eluent was evaporated

Sources & evidence

ORD record
ord-15658a642ce44120aa8138893167b7d4
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

Loading…