Dimethyl Sulfate → HCID 14800158, compound

HRID 728340Notes

Reaction equation

HRID 728340 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([OH:18])=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[C:15]([C:24]([O:26][CH3:27])=[O:25])=[N:14]1.[H-].[Na+].S(OC)(O[CH3:34])(=O)=O>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([O:18][CH3:34])=[C:16]([S:19][C:20]([F:21])([F:22])[F:23])[C:15]([C:24]([O:26][CH3:27])=[O:25])=[N:14]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 178499159HCID 178499159, compound

Product 1

HCID 14800158HCID 14800158, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A suspension of 5.8 g (0.013 mole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methoxycarbonyl-4-trifluoromethylsulfenyl-5-hydroxypyrazole and 0.37 g (0.015 mole) sodium hydride in 150 ml of dioxane was heated to reflux for 0.5 hr. during which time the color changed from brown to orange with evolution of gas. To the cooled mixture was added 1.94 g (0.015 mole) of dimethyl sulfate diluted in 10 ml of dioxane. The mixture was heated again to reflux for 1 hr. It was then cooled, the solids were filtered off and the filtrate was concentrated. The brown oil was taken up in dichloromethane and washed with water. The organic layer was dried and concentrated to afford 3.8 g (62.4 percent yield) of a brown oil. Purification by column chromatography using silica gel gave a solid, m.p. 97°-98° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 0.5 hr
  3. temperatureThe mixture was heated again
  4. temperatureto reflux for 1 hr
  5. temperatureIt was then cooled
  6. filtrationthe solids were filtered off
  7. concentrationthe filtrate was concentrated
  8. washwashed with water
  9. customThe organic layer was dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f18fba22a12f4880a1838e4b1254a478
Source dataset
uspto-grants-1991_09
Patent number
US05047550

Reaction notes

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