Dimethyl Sulfate → 2-Methyl-3,4,5-trichloroisothiazolium methylsulfate

HRID 1065123Notes

Reaction equation

HRID 1065123 reaction equation
[Cl:1][C:2]1[S:6][N:5]=[C:4]([Cl:7])[C:3]=1[Cl:8].[S:9]([O:14]C)([O:12][CH3:13])(=[O:11])=[O:10]>CCOCC>[CH3:13][O:12][S:9]([O-:14])(=[O:11])=[O:10].[CH3:13][N+:5]1[S:6][C:2]([Cl:1])=[C:3]([Cl:8])[C:4]=1[Cl:7]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 12333154Trichloroisothiazole

Product 1

HCID 128890232-Methyl-3,4,5-trichloroisothiazolium methylsulfate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trichloroisothiazole (37.7 g, 0.20 mol) and dimethyl sulfate (9.5 ml, 0.1 mol) were mixed under a nitrogen atmosphere. The mixture was heated at 135°-140° for 1 hr. The reaction mixture was cooled and poured into 100 ml of ether. The resulting solid was collected and washed with warm glyme to yield 14.5 g, (46%), mp 130°. The NMR and IR were consistent with the assigned structure.

Workup

  1. temperatureThe mixture was heated at 135°-140° for 1 hr
  2. temperatureThe reaction mixture was cooled
  3. customThe resulting solid was collected
  4. washwashed with warm glyme
  5. customto yield 14.5 g, (46%), mp 130°

Sources & evidence

ORD record
ord-138090ce3f5649babd61bb0ef918afc5
Source dataset
uspto-grants-1982_05
Patent number
US04328347

Reaction notes

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