Water → HCID 18965314, Verbindung

HRID 2226738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226738
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28]Cl.O>C(OCCCC)CCC.ClCCl>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Komponenten

7

Edukt 4

HCID 962WaterHCID 7108PhenothiazineHCID 24758Sodium hydrideHCID 109657372-[2-(2-Chloroethoxy)ethoxy]oxane

Produkt 1

HCID 18965314HCID 18965314, VerbindungAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8909Butyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

Phenothiazine (3.8 g, 19 mmol) was added to a suspension of sodium hydride (0.92 g, 23 mmol, 60% oil dispersion) in dry dibutylether (25 ml) under an atmosphere of nitrogen. The mixture was heated at 135° C. for 1 h and then cooled to approximately 100° C. 2-(2-((tetrahydro-2-pyranyl)oxy)ethoxy)ethylchloride (8 g, 38 mmol) was added in one portion and the mixture was heated overnight at 110° C. The reaction mixture was poured into water (250 ml) and extracted with dichloromethane (3×50 ml) and diethyl ether (50 ml). The combined organic extracts were washed with brine and dried over sodium sulphate. The solvent was evaporated in vacuo leaving an oil, which was submitted to column chromatography using dichloromethane as eluent. Collecting the proper fractions afforded 3.9 g of crude 10-(2-(2-((tetrahydro-2-pyranyl)oxy)ethoxy)ethyl)-10H-phenothiazine. TLC: rf=0.72 (SiO2 ; dichloromethane/methanol=19:1).

Aufarbeitung

  1. temperaturecooled to approximately 100° C
  2. temperaturethe mixture was heated overnight at 110° C
  3. extractionextracted with dichloromethane (3×50 ml) and diethyl ether (50 ml)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulphate
  6. customThe solvent was evaporated in vacuo
  7. customleaving an oil, which
  8. customCollecting the proper fractions

Quellen und Nachweise

ORD-Eintrag
ord-d6041f89af2f4048ba1c3adb14d74cf5
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05348965

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