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

HRID 49407

Reaction equation

HRID 49407 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 12115370Methyl 2-cyano-3-(3,4-dichloro-5-isothiazolyl)-3-oxopropanoateYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9ff7649d71484e3191a1ce31b2bc2cba
Source dataset
uspto-grants-2004_03
Patent number
US06706748B2

Linked notes

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