Malononitrile → 4-Chloro-3-dicyanomethylene-5-ethoxycarbonyl-2-methyl-4-isothiazoline

HRID 1980365Notes

Reaction equation

HRID 1980365 reaction equation
FS([O-])(=O)=O.Cl[C:7]1[C:11]([Cl:12])=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:9][N+:8]=1[CH3:18].[C:19](#[N:23])[CH2:20][C:21]#[N:22]>C(O)(C)C>[Cl:12][C:11]1[C:7](=[C:20]([C:19]#[N:23])[C:21]#[N:22])[N:8]([CH3:18])[S:9][C:10]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 8010MalononitrileHCID 128890133,4-Dichloro-2-methyl-5-ethoxycarbonylisothiazolium fluorosulfonate

Product 1

HCID 128890454-Chloro-3-dicyanomethylene-5-ethoxycarbonyl-2-methyl-4-isothiazolineYield 44%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3,4-Dichloro-5-ethoxycarbonyl-2-methylisothiazolium fluorosulfonate (7.5 g, 0.022 mole) was dissolved in 75 ml of isopropanol. Malononitrile (1.5 g, 0.023 mol) was added the mixture stirred for 30 min. The yellow solid was collected and washed with isopropanol to yield 2.6 g (44%) of product, mp 134-136. Analysis calculated for C10H8ClN3O2S2 : C 44.51; H, 3.00; Cl, 13.16; N, 15.57; S, 11.90. Found: C, 44.34; H, 2.82; Cl, 12.60; N, 14.82; S, 11.42.

Workup

  1. customThe yellow solid was collected
  2. washwashed with isopropanol

Sources & evidence

ORD record
ord-2492b366b96b4588ae842f9fa2993b32
Source dataset
uspto-grants-1985_04
Patent number
US04508908

Reaction notes

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