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

HRID 1065133Notes

Reaction equation

HRID 1065133 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:24])([F:23])[S:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:13])=[O:12]>CCOCC>[F:9][C:10]([F:24])([F:23])[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][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 10869071Octyl triflateHCID 12333154Trichloroisothiazole

Product 1

HCID 145357092-Octyl-3,4,5-trichloroisothiazolium trifluoromethane sulfonateYield 31%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trichloroisothiazole (6.6 g, 0.035 mol) and n-octyl trifluoromethane sulfonate (7.5 g, 0.0286 ml) were heated at 110° for 2 hrs. After cooling, 150 ml of ether was added and solution cooled in a dry ice/acetone bath. The ether was decanted and the brown oil dried to yield 4.0 g (31%) of product. Spectral data (NMR and IR) were consistent with the assigned structure.

Workup

  1. temperatureAfter cooling
  2. temperaturesolution cooled in a dry ice/acetone bath
  3. customThe ether was decanted
  4. customthe brown oil dried

Sources & evidence

ORD record
ord-d55342daf06f44509d256b92f43648af
Source dataset
uspto-grants-1982_05
Patent number
US04328347

Reaction notes

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