Dimethyl Sulfate → HCID 23042093, compound

HRID 2166090Notes

Reaction equation

HRID 2166090 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11](=[O:24])[N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[N:13]=1.S(OC)(O[CH3:29])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:10]=[C:11]([O:24][CH3:29])[N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:21])[F:22])[N:13]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 135616215HCID 135616215, compound

Product 1

HCID 23042093HCID 23042093, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.75 g (11.0 mmol) of 5-(2,6-difluorophenyl)-2-(α,α,α-trifluoro-o-tolyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 1.05 g (11.0 mmol) of dimethyl sulfate and 3.04 g (22.0 mmol) of potassium carbonate in acetone is stirred at the reflux temperature for 16 hours. The insoluble constituents are then filtered off and the evaporated residue is subjected to chromatography on silica gel using ethyl acetate/n-hexane (1:4) as the eluent. As the first fraction there is isolated the apolar secondary component 3-(2,6-difluorophenyl)-5-methoxy-1-(α,α,α-trifluoro-o-tolyl)-1H-1,2,4-triazole, m.p. 118°-119° C.; mass spectrum: 355(75), 298(39), 159(100); 1H-NMR (CDCl3): 4.13 (s, OCH3). After further elution with ethyl acetate/n-hexane (2:3) and subsequent recrystallization from diethyl ether/n-hexane there is obtained pure 5-(2,6-difluorophenyl)-4-methyl-2-(α,α,α-trifluoro-o-tolyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, m.p. 98°-99° C., IR spectrum: 1708 cm-1 ; mass spectrum: 355(75), 298(32), 159(100); 1H-NMR (CDCl3): 3.30 (s,N-CH3).

Workup

  1. filtrationThe insoluble constituents are then filtered off

Sources & evidence

ORD record
ord-408a60055b71497cbaa4735fc9117564
Source dataset
uspto-grants-1990_07
Patent number
US04943583

Reaction notes

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