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

HRID 1065135Notes

Reaction equation

HRID 1065135 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 C10H8ClN3O2SO2 : 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-ed1c409f210a494788c77206db5fce2c
Source dataset
uspto-grants-1982_05
Patent number
US04328347

Reaction notes

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