Water → HCID 12922309, compound

HRID 1658388Notes

Reaction equation

HRID 1658388 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[OH:6][C:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N+:10]([CH3:18])[N:9]([CH3:19])[C:8]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+].[CH3:28]I.O>CS(C)=O>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH3:28][O:6][C:7]1[C:8]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N+:9]([CH3:19])[N:10]([CH3:18])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 21398088HCID 21398088, compound

Product 1

HCID 12922309HCID 12922309, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
60 °C

Procedure

4-Hydroxy-1,2-dimethyl-3,5-diphenylpyrazolium perchlorate (7 g, 0.02 mole) in DMSO (2.5 ml) is added to 5% sodium hydroxide (0.84 g, 0.02 mole) in DMSO (100 ml), dropwise with stirring. The mixture is warmed to 60°C for 5 minutes, then stirred at room temperature for 4 hours. The reaction mixture (75 ml) is treated with methyl iodide (0.43 g, 0.013 mole) and the mixture is stirred at room temperature for 16 hours, then heated at 40°C for 2 hours. On pouring into water, a solid precipitates with melting point 88°C. One crystallization from methanol gives the product with melting point 132°-132.5°C in 53% yield.

Workup

  1. stirringstirred at room temperature for 4 hours
  2. stirringthe mixture is stirred at room temperature for 16 hours
  3. temperatureheated at 40°C for 2 hours
  4. customa solid precipitates with melting point 88°C
  5. customOne crystallization from methanol
  6. customgives the product with melting point 132°-132.5°C in 53% yield

Sources & evidence

ORD record
ord-f82809e81ba34055b5aec2a773a9396d
Source dataset
uspto-grants-1976_06
Patent number
US03963742

Reaction notes

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