Methanol → Difenzoquat metilsulfate

HRID 1457300Notes

Reaction equation

HRID 1457300 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:3]1.[CH3:19]O.[S:21](=[O:25])(=[O:24])([OH:23])[OH:22]>>[CH3:19][O:24][S:21]([O-:23])(=[O:22])=[O:25].[CH3:1][N+:2]1[N:3]([CH3:19])[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 887Methanol3×HCID 1118Sulfuric AcidHCID 1405171-Methyl-3,5-diphenylpyrazole

Product 1

HCID 39424Difenzoquat metilsulfateYield 91.8%

Conditions

Temperature
60 °C

Procedure

46.8 g (0.2 mol) of 1-methyl-3,5-diphenylpyrazole together with 40 g (1.25 mol) of methanol are introduced into the reaction vessel. After 22.5 g (0.22 mol) of 96% strength sulfuric acid have been added, the reaction solution is brought to 160° C. by distilling off methanol. 608 g (19 mol) of methanol are metered in below the surface of the reaction mixture in the course of 7.5 hours. After the mixture has cooled to 60° C., 10 g (0.31 mol) of methanol are added, and the mixture is cooled down to 10° C. At this temperature, the crystal slurry which has precipitated is filtered off. 68.1 g of 1,2-dimethyl-3,5-diphenylpyrazolium methylsulfate with a content of 97.3% (HPLC) of m.p. 157°-159° C. are obtained, which corresponds to a yield of 91.8% of theory.

Workup

  1. customis brought to 160° C.
  2. distillationby distilling off methanol
  3. customare metered in below the surface of the reaction mixture in the course of 7.5 hours
  4. temperaturethe mixture is cooled down to 10° C
  5. customAt this temperature, the crystal slurry which has precipitated
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-b04a5ab67a064a6a930610ad90d2418a
Source dataset
uspto-grants-1998_12
Patent number
US05847154

Reaction notes

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