Potassium Fluoride → HCID 19882832, compound

HRID 846523Notes

Reaction equation

HRID 846523 reaction equation
[F-].[K+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH3:12])=[CH:6][C:5]=1[N:13]1[C:17](=[O:18])[N:16]([CH2:19][CH2:20]OS(C)(=O)=O)[N:15]=[N:14]1>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH3:12])=[CH:6][C:5]=1[N:13]1[C:17](=[O:18])[N:16]([CH:19]=[CH2:20])[N:15]=[N:14]1

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 19882818HCID 19882818, compound

Product 1

HCID 19882832HCID 19882832, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 0.38 g (0.0066 mole) of potassium fluoride and 0.85 g (0.0022 mole) of 1-(2,4-dichloro-5-methoxyphenyl)-1,4-dihydro-4-[2(methylsulfonyloxy)ethyl]-5H-tetrazol-5-one in 35 mL of N,N-dimethylformamide was heated at 120°-130° C. for 2 hours, then stirred at room temperature for 3 days. The reaction mixture was poured into ice water then extracted with diethyl ether. The ether extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave a residue. The residue was purified by column chromatography on silica gel, eluting with methylene chloride, then recrystallized from ethyl acetate:heptane to yield 0.25 g of 1-(2,4-dichloro-5-methoxyphenyl)-4-ethenyl-1,4-dihydro-5H-tetrazol-5-one, mp 142°-143° C.

Workup

  1. temperaturewas heated at 120°-130° C. for 2 hours
  2. extractionthen extracted with diethyl ether
  3. extractionThe ether extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customto leave a residue
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with methylene chloride
  10. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3afddb7c84964e76ae96259672e43fe4
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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