Hexane → Ethyl alpha-nitro-9H-thioxanthene-9-acetate

HRID 258191

Reaktionsgleichung

Reaktionsgleichung von HRID 258191
O[CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[N+:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17].CCCCCC.[OH-].[K+]>O.C(O)C.CC(O)C>[N+:16]([CH:19]([CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17]

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 14797Potassium HydroxideHCID 69379Ethyl nitroacetateHCID 51541709H-thioxanthen-9-ol

Produkt 1

HCID 15290759Ethyl alpha-nitro-9H-thioxanthene-9-acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Crude 9-hydroxythioxanthene (9.58 g, 45 mmol) is mixed with ethyl nitroacetate (5.5 mL, 49 mmol) and heated at 100° C. for 1 hour. TLC (SiO2, hexane:2-propanol/3:1) after 45 minutes shows no starting material. The cooled reaction mixture is treated with 100 mL of ethanol and 39 mL of 1.25 M ethanolic potassium hydroxide solution. Ethanol is stripped and the residue taken up in water and extracted with diethyl ether. The aqueous layer is acidified to pH 2 to 3 with 85% phosphoric acid solution and refrigerated overnight. A crystalline solid is collected by filtration and dried at 50° C./10 mm Hg. A total of 8.4 g of the title compound is collected in three crops; mp 111°-115° C.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. extractionextracted with diethyl ether
  3. filtrationA crystalline solid is collected by filtration
  4. customdried at 50° C./10 mm Hg
  5. customA total of 8.4 g of the title compound is collected in three crops

Quellen und Nachweise

ORD-Eintrag
ord-5692cc207ef046b3ad5043b7e9a3a092
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264577

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