Methyl fluorosulfate → 2-Methyl-3,4,5-trichloroisothiazolium fluorosulfonate

HRID 1905033Notes

Reaction equation

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

Participants

Reactant 2

HCID 9870Methyl fluorosulfate

HCID 12333154Trichloroisothiazole

Product 1

HCID 128890222-Methyl-3,4,5-trichloroisothiazolium fluorosulfonateYield 96%

Procedure

Trichloroisothiazole (37.7 g, 0.20 mol) and 38 ml of methyl fluorosulfonate were mixed under a nitrogen atmosphere. The mixture was heated at 70°-80° for 30 min. The resulting solid was washed with ether and benzene to yield 55.6 g (96%) of 2-methyl-3,4,5-trichloroisothiazolium fluorosulfonate, mp 162 (d). Analysis calculated for C4H3Cl3FNO3S2 : C, 15.87; H, 0.99; N, 4.63; Found: C, 15.81; H, 1.02; N, 4.49.

Workup

temperatureThe mixture was heated at 70°-80° for 30 min
washThe resulting solid was washed with ether and benzene

Sources & evidence

ORD record: ord-050ab187ea7c40d6a5da5c3b64075d12
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04841063

Reaction notes

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