Methyl fluorosulfate → 5-Cyano-3,4-dichloro-2-methyl isothiazolium fluorosulfonate

HRID 1065129Notes

Reaction equation

HRID 1065129 reaction equation
[C:1]([C:3]1[S:7][N:6]=[C:5]([Cl:8])[C:4]=1[Cl:9])#[N:2].[F:10][S:11]([O:14][CH3:15])(=[O:13])=[O:12]>>[F:10][S:11]([O-:14])(=[O:13])=[O:12].[C:1]([C:3]1[S:7][N+:6]([CH3:15])=[C:5]([Cl:8])[C:4]=1[Cl:9])#[N:2]

Participants

3

Reactant 2

HCID 9870Methyl fluorosulfateHCID 19738264Dichloro-1,2-thiazole-5-carbonitrile

Product 1

HCID 128890295-Cyano-3,4-dichloro-2-methyl isothiazolium fluorosulfonateYield 77%

Procedure

5-Cyano-3,4-dichloroisothiazole (3.6 g, 0.02 mol) and 4 ml of methyl fluorosulfonate were heated at 80°-100° for 11/2 hrs under a nitrogen atmosphere. The resulting solid was washed with ether and benzene to yield 4.5 g (77%) of 5-cyano-3,4-dichloro-2-methyl isothiazolium fluorosulfonate, mp 163-174 (d). Spectral data (NMR and IR) were consistent with the assigned structure.

Workup

  1. washThe resulting solid was washed with ether and benzene

Sources & evidence

ORD record
ord-bc25c9a08f164adfa8b7a42e86a0fb86
Source dataset
uspto-grants-1982_05
Patent number
US04328347

Reaction notes

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