Hydrochloric Acid → Methyl 2-cyano-3-(3,4-dichloro-5-isothiazolyl)-3-oxopropanoate

HRID 49407

Reaktionsgleichung

Reaktionsgleichung von HRID 49407
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[Cl:8][C:9]1[C:13]([Cl:14])=[C:12]([C:15](Cl)=[O:16])[S:11][N:10]=1.Cl>O1CCCC1>[C:1]([CH:3]([C:15]([C:12]1[S:11][N:10]=[C:9]([Cl:8])[C:13]=1[Cl:14])=[O:16])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 7747Methyl cyanoacetateHCID 109768863,4-Dichloro-5-isothiazolecarbonyl chloride

Produkt 1

HCID 12115370Methyl 2-cyano-3-(3,4-dichloro-5-isothiazolyl)-3-oxopropanoateAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of methyl cyanoacetate (1.98 g) in unhydrous tetrahydrofuran (20 ml) 60% sodium hydride (1.6 g) was added at a temperature below 10° C. To the reaction mixture a solution of 3,4-dichloro-5-isothiazolecarbonyl chloride (4.30 g) in unhydrous tetrahydrofuran (15 ml) was added dropwise at the same temperature. After finishing the addition, the reaction mixture was stirred at room temperature for 2 hours and 1N-aqueous hydrochloric acid (10 ml) was added. After extraction with ethyl acetate and drying the organic phase with unhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain methyl 2-cyano-3-(3,4-dichloro-5-isothiazolyl)-3-oxopropanoate (4.7 g) as pale yellow crystals. mp 119-122° C.

Aufarbeitung

  1. additionthe addition
  2. extractionAfter extraction with ethyl acetate
  3. dry with materialdrying the organic phase with unhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9ff7649d71484e3191a1ce31b2bc2cba
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706748B2

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