Sodium Chloride → HCID 12388583, compound

HRID 1390345Notes

Reaction equation

HRID 1390345 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([N:7]2[N:11]=[C:10]([OH:12])[CH:9]=[N:8]2)=[CH:3][CH:2]=1.[OH-].[Na+].S(OC)(O[CH3:20])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>C(Cl)Cl.O>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([N:7]2[N:11]=[C:10]([O:12][CH3:20])[CH:9]=[N:8]2)=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 178426275HCID 178426275, compound

Product 1

HCID 12388583HCID 12388583, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

With efficient stirring, 71.5 g of 2-p-tolyl-4-hydroxy-2H-1,2,3-triazole (m.p. 178°-180° C., prepared in accordance with Synthesis 1974 (March), pp. 198-199) are added at room temperature to a mixture of 350 ml of water and 25 g of sodium hydroxide. After half an hour, 64 g of dimethyl sulphate are added dropwise to the reaction mixture over a period of half an hour, in the course of which time the reaction temperature rises to approx. 40° C. and a slighly brownish coloured emulsion forms. After the exothermic reaction has subsided, the mixture is heated for 1 hour to 50°-55° C., then 10 g of calcined sodium carbonate are added and the methylation product is expelled with steam. To the distillate is added 10% sodium chloride and the oily product is taken up in methylene chloride, dried over magnesium sulphate and the solvent is distilled off after filtration. Distillation in vacuo yields 50 g of 2-p-tolyl-4-methoxy- 2H-1,2,3-triazole (b.p. 145°-149° C.) as a slightly yellowish liquid.

Workup

  1. waitAfter half an hour
  2. customrises to approx. 40° C.
  3. customAfter the exothermic reaction
  4. temperaturethe mixture is heated for 1 hour to 50°-55° C.
  5. dry with materialdried over magnesium sulphate
  6. distillationthe solvent is distilled off
  7. filtrationafter filtration
  8. distillationDistillation in vacuo

Sources & evidence

ORD record
ord-511cc07bb2394398b2da9ba65aa75ea6
Source dataset
uspto-grants-1979_02
Patent number
US04138552

Reaction notes

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