Ethanol → 4-chloro-2-fluorophenyl-1,4-dihydro-5H-tetrazol-5-one

HRID 1608040Notes

Reaction equation

HRID 1608040 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](SCC)=[N:12][N:11]=[N:10]2)=[C:5]([F:17])[CH:4]=1.C([OH:20])C>O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:20])[NH:12][N:11]=[N:10]2)=[C:5]([F:17])[CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5360545SodiumHCID 14551620(1-(4-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)ethyl sulfide

Product 1

HCID 1356217974-chloro-2-fluorophenyl-1,4-dihydro-5H-tetrazol-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 0.12 g (0.0052 mole) of sodium in 16 ml of ethanol was added 1.2 g (0.0046 mole) of (1-(4-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)ethyl sulfide. The resultant solution was heated at reflux for six hours. The reaction mixture was cooled and the solvent was evaporated under reduced pressure leaving a residue. This residue was dissolved in 40 ml of water and the aqueous solution was washed with diethyl ether. The aqueous phase was acidified with concentrated hydrochloric acid forming a precipitate. The precipitate was collected by filtration and dried to yield 0.55 g of 1-(4-chloro-2-fluorophenyl)-1,4-dihydro-5H-tetrazol-5-one as a solid, m.p. 194° C.

Workup

  1. temperatureat reflux for six hours
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was evaporated under reduced pressure
  4. customleaving a residue
  5. washthe aqueous solution was washed with diethyl ether
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-15de671adb30457e943adb52c6c8b5ce
Source dataset
uspto-grants-1989_09
Patent number
US04868321

Reaction notes

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