Potassium Iodide → 1,4-dihydro-1-(2-iodoethyl)-4-methyl-5H-tetrazol-5-one

HRID 1863030Notes

Reaction equation

HRID 1863030 reaction equation
[I:1]C.Cl[CH2:4][CH2:5][N:6]1[C:10](=O)[NH:9][N:8]=[N:7]1.[C:12](=[O:15])([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[I:1][CH2:4][CH2:5][N:6]1[C:12](=[O:15])[N:9]([CH3:10])[N:8]=[N:7]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 1358293471-(2-chloroethyl)-1,4-dihydro-5H-tetrazol-5-one

Product 1

HCID 136767191,4-dihydro-1-(2-iodoethyl)-4-methyl-5H-tetrazol-5-oneYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 49 parts of iodomethane, 10.5 parts of 1-(2-chloroethyl)-1,4-dihydro-5H-tetrazol-5-one, 15 parts of sodium carbonate, 0.2 parts of potassium iodide and 240 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is cooled, 100 parts of water are added and the layers are separated. The aqueous phase is extracted with dichloromethane. The combined organic phases are dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding 15 parts (85%) of 1,4-dihydro-1-(2-iodoethyl)-4-methyl-5H-tetrazol-5-one as a residue.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe layers are separated
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. customThe combined organic phases are dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated

Sources & evidence

ORD record
ord-ca68393763014a85a584fef82393eec1
Source dataset
uspto-grants-1979_09
Patent number
US04167574

Reaction notes

Loading…