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

HRID 1065128Notes

Reaction equation

HRID 1065128 reaction equation
[C:1]([C:3]1[C:4]([Cl:9])=[N:5][S:6][C:7]=1[Cl:8])#[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[C:4]([Cl:9])=[N+:5]([CH3:15])[S:6][C:7]=1[Cl:8])#[N:2]

Participants

3

Reactant 2

HCID 9870Methyl fluorosulfateHCID 305706Dichloro-1,2-thiazole-4-carbonitrile

Product 1

HCID 128890284-Cyano-3,5-dichloro-2-methylisothiazolium fluorosulfonateYield 92%

Procedure

4-Cyano-3,5-dichloroisothiazole (5.0 g, 0.028 mol) and 4 ml of methyl fluorosulfonate were heated at 80°-90° for 30 min under a nitrogen atmosphere. The resulting solid was washed with ether and benzene to yield 7.5 g (92%) of 4-cyano-3,5-dichloro-2-methylisothiazolium fluorosulfonate, mp 160-170. Spectral data (NMR and IR) were consistent with the assigned structure. Analysis--Calculated for C5H3Cl2FN2O3S2 : C, 20.50; H, 1.02; Found: C, 20.27; H, 1.44.

Workup

  1. washThe resulting solid was washed with ether and benzene

Sources & evidence

ORD record
ord-60fda5dbcdc749f5ac9eed283d0a485c
Source dataset
uspto-grants-1982_05
Patent number
US04328347

Reaction notes

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