Iodoethane → N-Ethylphenothiazine

HRID 268576

Reaktionsgleichung

Reaktionsgleichung von HRID 268576
[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.I[CH2:16][CH3:17].[OH-].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:16]([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)[CH3:17]

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 7108PhenothiazineHCID 14797Potassium Hydroxide

Produkt 1

HCID 219178N-Ethylphenothiazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 10 g (0.05 mol) of phenothiazine (obtained from Fluka), 11.7 g (0.075 mol) of iodoethane (obtained from Aldrich), 4.2 g (0.075 mol) of potassium hydroxide and 0.25 g of tetra-n-butylammonium hydrogen sulfate (obtained from Aldrich) in 200 ml of dry toluene was refluxed for 24 hours. After cooling, the reaction mixture was filtered and the solvent was evaporated. The product was recrystallized from methanol. The yield of 10-ethylphenothiazine (C14H13NS, FW=227.33) was 90%. The melting point of the product was 103-104° C. The 1H-NMR spectrum (100 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 1.40 (t, J=7.0 Hz, 3H, CH3); 3.90 (q, J=7.0 Hz, 2H, CH2); 6.78-7.32 (m, 8H, Ar).

Aufarbeitung

  1. temperaturewas refluxed for 24 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe solvent was evaporated
  5. customThe product was recrystallized from methanol
  6. customwas 103-104° C

Quellen und Nachweise

ORD-Eintrag
ord-5dca1ffcee9c4e1fac40ef9667593d59
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07445877B2

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