Methanol → Difenzoquat metilsulfate

HRID 1457299Notes

Reaction equation

HRID 1457299 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]>ClCCCl>[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

5

Reactant 3

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 1405171-Methyl-3,5-diphenylpyrazole

Product 1

HCID 39424Difenzoquat metilsulfateYield 91.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °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 19.4 g (0.19 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 been cooled to 70° C., 25 g of 1,2-dichloroethane are added, and the mixture is cooled to room temperature with stirring. The reaction mixture is filtered and washed with 12.5 g of 1,2-dichloroethane. 67.7 g of 1,2-dimethyl-3,5-diphenylpyrazolium methylsulfate with a content of 97.5% (HPLC) of m.p. 157°-159° C. are obtained, which corresponds to a yield of 91.7% 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 to room temperature
  5. filtrationThe reaction mixture is filtered
  6. washwashed with 12.5 g of 1,2-dichloroethane

Sources & evidence

ORD record
ord-5622c04bb79143c7bf771a1e6edfa8d4
Source dataset
uspto-grants-1998_12
Patent number
US05847154

Reaction notes

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