2,3-Dichloropropene → HCID 21875394, Verbindung

HRID 1441806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441806
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[SH:11].[Cl:12][C:13]([CH2:15]Cl)=[CH2:14].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11][CH2:15][C:13]([Cl:12])=[CH2:14]

Komponenten

7

Edukt 4

HCID 65652,3-DichloropropeneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 47130122-chloro-5-nitrobenzenethiol

Produkt 1

HCID 21875394HCID 21875394, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 2-chloro-5-nitro-benzenethiol (1.0 g, 5.27 mmol, prepared in accordance with the procedure described by Still et al. Synth. Comm. 13, 1181 (1983)) in 15 mL DMF was treated with 2,3-dichloropropene (693 μL, 7.52 mmol) and K2CO3 (433 mg, 3.13 mmol). The mixture was heated at 80° C. for 2 h and then allowed to cool to rt. EtOAc (200 mL) and H2O (100 mL) were added. The organic phase was washed with H2O (2×250 mL), saturated aqueous NaCl (100 mL), dried over MgSO4, and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel eluting with 20% EtOAc in hexanes to give compound 260A (1.09 g, 89%) as an orange oil.

Aufarbeitung

  1. temperatureto cool to rt
  2. washThe organic phase was washed with H2O (2×250 mL), saturated aqueous NaCl (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash column chromatography on silica gel eluting with 20% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-85ca8677847f47aeb437bb00412db972
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655689B2

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