Potassium Iodide → 1-(2-Chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one

HRID 1863029Notes

Reaction equation

HRID 1863029 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[NH:6][N:5]=[N:4]1)[CH3:2].Br[CH2:10][CH2:11][Cl:12].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[Cl:12][CH2:11][CH2:10][N:6]1[C:7](=[O:8])[N:3]([CH2:1][CH3:2])[N:4]=[N:5]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 78491-Bromo-2-ChloroethaneHCID 10340Sodium CarbonateHCID 1354729431-ethyl-1,2-dihydro-5H-tetrazol-5-one

Product 1

HCID 30179061-(2-Chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-oneYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 22 parts of 1-ethyl-1,4-dihydro-5H-tetrazol-5-one, 45 parts of 1-bromo-2-chloroethane, 26 parts of sodium carbonate, 0.3 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, water is added and the layers are separated. The aqueous phase is extracted three times 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 28.4 parts (80%) of 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-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 three times 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-ce20713baa6a4b1aa6d434c8f989b2a8
Source dataset
uspto-grants-1979_09
Patent number
US04167574

Reaction notes

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