Dimethyl Sulfate → Difenzoquat metilsulfate

HRID 426564Notes

Reaction equation

HRID 426564 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:20][S:21]([O:24]C)(=[O:23])=[O:22]>C1(C)C(C)=CC=CC=1>[CH3:19][O:20][S:21]([O-:24])(=[O:23])=[O:22].[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 2

HCID 6497Dimethyl SulfateHCID 1405171-Methyl-3,5-diphenylpyrazole

Product 1

HCID 39424Difenzoquat metilsulfateYield 88%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

375 Grams (1.6 moles) of 1-methyl-3,5-diphenylpyrazole is dissolved in 1850 ml. of dry xylene and heated to 60° C. 208.13 Grams (1.65 moles) of dimethylsulfate in 150 ml. of dry xylene is then added and the temperature of the reaction mixture raised to 105° C. to 110° C. and maintained there for 7.5 hours. The mixture is allowed to cool and then filtered. A brown solid is recovered, washed with xylene and then dry acetone to give the product in 88% yield, having a melting point of 155° C. to 157° C.

Workup

  1. temperaturethe temperature of the reaction mixture raised to 105° C. to 110° C.
  2. temperaturemaintained there for 7.5 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. customA brown solid is recovered
  6. washwashed with xylene
  7. customdry acetone to give the product in 88% yield

Sources & evidence

ORD record
ord-f7fab7d8afc449479e59dcfbaebe297a
Source dataset
uspto-grants-1979_10
Patent number
US04170464

Reaction notes

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