Isopropyl iodide → HCID 19882802, compound

HRID 846510Notes

Reaction equation

HRID 846510 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][CH3:18])[N:12]=[N:11]1.C(=O)([O-])[O-].[K+].[K+].I[CH:26]([CH3:28])[CH3:27]>CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH:26]([CH3:28])[CH3:27])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][CH3:18])[N:12]=[N:11]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 14349357HCID 14349357, compound

Product 1

HCID 19882802HCID 19882802, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 0.87 g (0.0034 mole) of 1-(2,4-difluoro-5-hydroxyphenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one, 0.7 g (0.0051 mole) of potassium carbonate, and 1.2 g (0.007 mole) of 2-iodopropane in 40 mL of acetone was heated at reflux for approximately 18 hours. The mixture was cooled, filtered, and the solvent evaporated under reduced pressure to leave an oil. The oil was purified by filtration through a small amount of silica gel followed by crystallization from heptane to yield 0.38 g of 1-[2,4-difluoro-5-(1-methylethoxy)phenyl]-1,4-dihydro-4-propyl-5H-tetrazol-5-one, mp 76.5°-77° C..

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 18 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customto leave an oil
  7. filtrationThe oil was purified by filtration through a small amount of silica gel
  8. customfollowed by crystallization from heptane

Sources & evidence

ORD record
ord-9c99c96c044c44a4934f6504d19f2568
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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