Sulfuric Acid → HCID 12388581, compound

HRID 1390347Notes

Reaction equation

HRID 1390347 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([N:7]2[N:11]=[C:10]([OH:12])[CH:9]=[N+:8]2[O-:13])=[CH:3][CH:2]=1.[C:15](=O)([O-])[O-].[K+].[K+].CI.S(=O)(=O)(O)O>CN(C)C=O.O>[C:1]1([CH3:14])[CH:2]=[CH:3][C:4]([N:7]2[N:11]=[C:10]([O:12][CH3:15])[CH:9]=[N+:8]2[O-:13])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178426282HCID 178426282, compound

Product 1

HCID 12388581HCID 12388581, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

81.4 g of 2-(p-tolyl)-4-hydroxy-2H-1,2,3-triazole-1-oxide (m.p. 150°-154° C. with decomp., prepared in accordance with Synthesis 1974 (March), pp. 198-199) are dissolved in 810 ml of dimethyl formamide at room temperature. Then 141.3 g of potassium carbonate are suspended in this solution and 48.3 ml of methyl iodide are poured into the suspension with good stirring. The batch is then heated to 60° C. over 30 minutes and kept thereat for 6 hours. The fine suspension is thereafter poured into 6 liters of water, and the pH is adjusted to 4-5 with 2N sulphuric acid. After cooling to room temperature, the solid is collected with suction, washed with water and dried to yield 56.5 g of 2-(p-tolyl)-4-methoxy-2H-1,2,3-triazole-1-oxide with a melting point of 62°-64° C. After recrystallisation from alcohol/water the product melts at 70°-72° C.

Workup

  1. custom, prepared in accordance with Synthesis 1974 (March)
  2. additionare poured into the suspension with good stirring
  3. temperatureAfter cooling to room temperature
  4. customthe solid is collected with suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-728c51ec472e466e9d3f6d378a6f067e
Source dataset
uspto-grants-1979_02
Patent number
US04138552

Reaction notes

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