2-Propen-1-yl 1,1,1-trifluoromethanesulfonate → 2-(2-Propen-1-yl)-3,4,5-trichloroisothiazolium trifluoromethane sulfonate

HRID 1065134Notes

Reaction equation

HRID 1065134 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][CH:16]=[CH2:17])(=[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].[CH2:17]([N+:5]1[S:6][C:2]([Cl:1])=[C:3]([Cl:8])[C:4]=1[Cl:7])[CH:16]=[CH2:15]

Participants

4

Reactant 2

HCID 109322232-Propen-1-yl 1,1,1-trifluoromethanesulfonateHCID 12333154Trichloroisothiazole

Product 1

HCID 130971832-(2-Propen-1-yl)-3,4,5-trichloroisothiazolium trifluoromethane sulfonateYield 30%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Trichloroisothiazole (5.7 g, 0.03 ml) and a solution of allyl trifluoromethane sulfonate (0.03 mol) in CCl4 were heated and excess CCl4 was removed by distillation until the reacting temperature reached 90° C. After heating at 90° for 30 min, the reaction was cooled and 150 ml of ether added. The solid was collected to yield 2.6 g (30%) of product, mp 103-105. Spectral data (NMR and IR) were consistent with the assigned structure.

Workup

  1. customexcess CCl4 was removed by distillation until the reacting temperature
  2. customreached 90° C
  3. temperatureAfter heating at 90° for 30 min
  4. temperaturethe reaction was cooled
  5. addition150 ml of ether added
  6. customThe solid was collected

Sources & evidence

ORD record
ord-facd532933f84d1c981d974f97b0cf05
Source dataset
uspto-grants-1982_05
Patent number
US04328347

Reaction notes

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