Iodoethane → N-Ethylphenothiazine

HRID 1375307

Reaktionsgleichung

Reaktionsgleichung von HRID 1375307
[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 (from Fluka), 11.7 g (0.075 mol) of iodoethane (from Aldrich), 4.2 g (0.075 mol) of potassium hydroxide, and 0.25 g of tetra-n-butylammonium hydrogen sulfate (from Aldrich) in 200 ml of dry toluene was refluxed for 24 hrs. The cooled reaction mixture was filtered and the solvent was evaporated. The product was recrystallized from methanol. The yield of 10-ethylphenothiazine was 10.2 g (90%). The product had a melting point of 103–104° C. (recrystallized from methanol). A 1H NMR spectrum yielded the following results (100 MHz, CDCl3, 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 hrs
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customthe solvent was evaporated
  5. customThe product was recrystallized from methanol
  6. customa melting point of 103–104° C. (recrystallized from methanol)
  7. customA 1H NMR spectrum yielded the
  8. customfollowing results (100 MHz, CDCl3, δ, ppm)

Quellen und Nachweise

ORD-Eintrag
ord-243b4f4bd18e4e9b86c3f72c39e5d38d
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169520B2

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