Carbon Disulfide → ethyl 2-(1,3-dithiol-2-ylidene)-2-[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate

HRID 977961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977961
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6](=[O:21])[N:7]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH3:2].[C:23](=[S:25])=[S:24].[OH-].[K+].Cl/[CH:29]=[CH:30]\Cl>CS(C)=O.O>[S:24]1[CH:30]=[CH:29][S:25][C:23]1=[C:5]([C:6](=[O:21])[N:7]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:4]([O:3][CH2:1][CH3:2])=[O:22]

Komponenten

7

Edukt 4

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 643833cis-1,2-DichloroethyleneHCID 53944986Ethyl[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate

Produkt 1

HCID 54216764ethyl 2-(1,3-dithiol-2-ylidene)-2-[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Ethyl[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (1.0 g) and carbon disulfide (0.2 ml) are dissolved in dimethylsulfoxide (12 ml), and thereto is added a solution of potassium hydroxide (378 mg) in water (1 ml). The mixture is stirred at room temperature for 20 minutes. A solution of cis-1,2-dichloroethylene (0.245 ml) in dimethylsulfoxide (2 ml) is added dropwise to the mixture, and the mixture is stirred at 50°-55° C. for 6 hours. After cooling, the mixture is poured into water, and the aqueous solution is extracted with ethyl acetate. The extract is washed with water, dried and then distilled to remove the solvent. The residue is purified by silica gel column chromatography (solvent, ethyl acetate) to give ethyl 2-(1,3-dithiol-2-ylidene)-2-[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (429 mg) as oil.

Aufarbeitung

  1. stirringthe mixture is stirred at 50°-55° C. for 6 hours
  2. temperatureAfter cooling
  3. extractionthe aqueous solution is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography (solvent, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0e0ced95a05f4a74ae1e18413bb072d7
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04663319

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