Tetrahydrofuran → N-{[2,3-dichloro-4-cyano-5-(3,4-dichlorophenyl)pyrrol-1-yl]methyl}acetamide

HRID 654132

Reaktionsgleichung

Reaktionsgleichung von HRID 654132
[Cl:1][C:2]1[C:3]([C:16]#[N:17])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[NH:5][C:6]=1[Cl:7].O1CCCC1.[H-].[Na+].C(O)(=O)C.O[CH2:30][NH:31][C:32](=[O:34])[CH3:33]>O.C(Cl)Cl.C(OCC)(=O)C.C(Cl)Cl>[Cl:7][C:6]1[N:5]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)=[C:3]([C:16]#[N:17])[C:2]=1[Cl:1]

Komponenten

8

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 1835554,5-dichloro-2-(3,4-dichlorophenyl)-1H-pyrrole-3-carbonitrileHCID 86745977N-(hydroxymethyl)acetamide acetate

Produkt 1

HCID 19888638N-{[2,3-dichloro-4-cyano-5-(3,4-dichlorophenyl)pyrrol-1-yl]methyl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

A slurry of 4,5-dichloro-2-(3,4-dichlorophenyl)pyrrole-3-carbonitrile (15.3 g, 0.05 mol) and tetrahydrofuran (80 mL) is cooled to 10° C. and treated portionwise over 20 minutes with sodium hydride (2.2 g, 60% in oil, 0.055 mol). After stirring for 15 minutes this solution is added dropwise to a 50° C. solution of N-(hydroxymethyl)acetamide acetate (ester) (9.18 g, 0.07 mol) and tetrahydrofuran (20 mL). The reaction mixture is refluxed for two hours, cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic extract is washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a solid. Flash chromatography of the solid on silica gel packed in methylene chloride using ethyl acetate/methylene chloride solutions as eluents gives a solid. Recrystallization of the solid from ethyl acetate gives the title product as off white crystals (5.35 g, mp 162°-162.5° C.) which is identified by IR and NMR spectral analyses.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for two hours
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a solid
  8. customgives a solid
  9. customRecrystallization of the solid from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-634bb40dd24547a7b237b95582161f04
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05130328

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