Dimethyl Sulfate → HCID 22749104, compound

HRID 1390346Notes

Reaction equation

HRID 1390346 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[N:13]=[C:12]([OH:14])[CH:11]=[N+:10]2[O-:15])[CH:5]=[CH:6][C:7]=1[CH3:8].[OH-].[K+].S(OC)(O[CH3:22])(=O)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[N:13]=[C:12]([O:14][CH3:22])[CH:11]=[N+:10]2[O-:15])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium Hydroxide2×HCID 178426283HCID 178426283, compound

Product 1

HCID 22749104HCID 22749104, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

113 g of 2-(3-chloro-4-methylphenyl)-4-hydroxy-2H-1,2,3-triazole-1-oxide (m.p. 166°-170° with decomp., prepared in accordance with Synthesis 1974 (March), pp. 189-199) are added at room temperature to a solution of 43 g of 85% potassium hydroxide in 750 ml of water. With efficient stirring, 79 g of dimethyl sulphate and simultaneously 55 ml of 30% potassium hydroxide solution are added to the reaction mixture in the course of 15 minutes while maintaining an internal temperature of 25°-35° C. by cooling. The batch is subsequently heated for 1 hour to 45°-50° C., and cooled to room temperature. The solid is then collected with suction, washed with water and dried. One crystallisation from isopropanol yields 30 g of 2-(3-chloro-4-methylphenyl)-4-methoxy-2H-1,2,3-triazole-1-oxide in the form of colourless crystals. Melting point: 106°-108° C.

Workup

  1. custom, prepared in accordance with Synthesis 1974 (March)
  2. temperaturewhile maintaining an internal temperature of 25°-35° C.
  3. temperatureby cooling
  4. temperatureThe batch is subsequently heated for 1 hour to 45°-50° C.
  5. customThe solid is then collected with suction
  6. washwashed with water
  7. customdried
  8. customOne crystallisation from isopropanol

Sources & evidence

ORD record
ord-542453c4017b48aeade399126a27b85e
Source dataset
uspto-grants-1979_02
Patent number
US04138552

Reaction notes

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