Methyl fluorosulfate → 3,4-Dichloro-2-methyl-5-ethoxycarbonylisothiazolium fluorosulfonate

HRID 1065130Notes

Reaction equation

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

Participants

Reactant 2

HCID 9870Methyl fluorosulfate

HCID 12889011Ethyl 3,4-dichloro-1,2-thiazole-5-carboxylate

Product 1

HCID 128890133,4-Dichloro-2-methyl-5-ethoxycarbonylisothiazolium fluorosulfonateYield 99%

Procedure

3,4-Dichloro-5-ethoxycarbonylisothiazole (6.0 g, 0.027 mol) and 4 ml of methyl fluorosulfonate were heated at 110° for 1 hr under a nitrogen atmosphere. The solid was washed with ether and benzene to yield 9.0 g (99%) of 3,4-dichloro-2-methyl-5-ethoxycarbonylisothiazolium fluorosulfonate, mp 118-123. Analysis--Calculated for C7H8Cl2FNO5S2 : Cl, 20.84; N, 4.12; S, 18.85. Found Cl, 20.56; N, 4.06; S, 18.89.

Workup

washThe solid was washed with ether and benzene

Sources & evidence

ORD record: ord-32138b6b873b4859888fe49f9412f31b
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04328347

Reaction notes

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