Propyl triflate → 2-Propyl-3,4,5-trichloroisothiazolium trifluoromethane sulfonate

HRID 1065132Notes

Reaction equation

HRID 1065132 reaction equation
[Cl:1][C:2]1[S:6][N:5]=[C:4]([Cl:7])[C:3]=1[Cl:8].[F:9][C:10]([F:19])([F:18])[S:11]([O:14][CH2:15][CH2:16][CH3:17])(=[O:13])=[O:12]>C(Cl)(Cl)(Cl)Cl>[F:9][C:10]([F:19])([F:18])[S:11]([O-:14])(=[O:13])=[O:12].[CH2:15]([N+:5]1[S:6][C:2]([Cl:1])=[C:3]([Cl:8])[C:4]=1[Cl:7])[CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 10965343Propyl triflateHCID 12333154Trichloroisothiazole

Product 1

HCID 130971822-Propyl-3,4,5-trichloroisothiazolium trifluoromethane sulfonateYield 28%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Trichloroisothiazole (4.7 g, 0.025 mol) and a solution of 0.02 mol of n-propyl trifluoromethane sulfonate in CCl4 were heated at 110° and CCl4 was removed via distillation. After heating at 110° for 11/2 hrs, the reaction was cooled and ether added. The ether was cooled in an ice bath and the solid collected to yield 2.1 g (28%) of product, mp 95°-99°. Analysis--Calculated for C7H7Cl3F3NO3S: C, 22.09; H, 1.86; Cl, 27.95; N, 3.68; S, 16.84. Found: C, 2160; H, 1.94; Cl, 27.15; N, 3.57; S, 16.27.

Workup

  1. customCCl4 was removed via distillation
  2. temperatureAfter heating at 110° for 11/2 hrs
  3. temperaturethe reaction was cooled
  4. additionether added
  5. temperatureThe ether was cooled in an ice bath
  6. customthe solid collected

Sources & evidence

ORD record
ord-3111ac717b474c2389521361c4b4f576
Source dataset
uspto-grants-1982_05
Patent number
US04328347

Reaction notes

Loading…