1-Chloromethyl-1H-1,2,4-triazole → Diethyl [(1H-1,2,4-triazol-1-yl)methyl]phosphonate

HRID 615065Notes

Reaction equation

HRID 615065 reaction equation
Cl[CH2:2][N:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[P:8]([O-:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11].[Na+]>C(#N)C>[N:3]1([CH2:2][P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])[CH:7]=[N:6][CH:5]=[N:4]1

Participants

4

Reactant 2

HCID 37438821-Chloromethyl-1H-1,2,4-triazoleHCID 23684067Sodium diethyl phosphite

Product 1

HCID 15145771Diethyl [(1H-1,2,4-triazol-1-yl)methyl]phosphonateYield 56.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 18.2 g (0.155 mole) of 1-chloromethyl-1H-1,2,4-triazole, 27.2 g (0.17 mole) of sodium diethyl phosphite and 200 ml of acetonitrile is heated for 2 hours to 60° C. and then refluxed for 16 hours. The precipitate is removed and the solution is concentrated. Fractional distillation of the residue yields 19.1 g (56.5%) of diethyl (1H-1,2,4-triazol-1-yl)methylphosphonate in the form of a colourless oil with a boiling point of 120°-129° C./0.053 mb.

Workup

  1. temperatureis heated for 2 hours to 60° C.
  2. temperaturerefluxed for 16 hours
  3. customThe precipitate is removed
  4. concentrationthe solution is concentrated
  5. distillationFractional distillation of the residue

Sources & evidence

ORD record
ord-3c08085d75ff4063baf47e8fb5a554e8
Source dataset
uspto-grants-1985_02
Patent number
US04497647

Reaction notes

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