Dimethylformamide → 10-Ethylphenothiazine-3-carbaldehyde

HRID 268577

Reaktionsgleichung

Reaktionsgleichung von HRID 268577
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:8]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:7].[OH-].[K+].CN(C)[CH:26]=[O:27]>>[CH2:6]([N:8]1[C:9]2[CH:10]=[CH:11][C:12]([CH:26]=[O:27])=[CH:13][C:14]=2[S:15][C:16]2[C:21]1=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:7]

Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 219178N-Ethylphenothiazine

Produkt 1

HCID 31433010-Ethylphenothiazine-3-carbaldehyde

Versuchsvorschrift

Phosphorus oxychloride (POCl3, 3.7 ml, 0.04 mol) (obtained from Aldrich) was added dropwise to 4.4 ml (0.06 mol) of dry dimethylformamide (DMF) at 0° C. under a nitrogen atmosphere. This solution was warmed up slowly to room temperature. Next, a solution of 5 g (0.02 mol) of 10-ethylphenothiazine in dry DMF was added dropwise. The reaction mixture was refluxed at 80° C. for 24 hours and poured into the ice water. This solution was neutralized with potassium hydroxide until the pH reached 6-8. The product was extracted with chloroform. The chloroform extract was dried over anhydrous sodium sulfate, filtered and distilled. The product was recrystallized from methanol. The yield of 10-ethylphenothiazine-3-carbaldehyde (C15H13NOS, FW=255.34) was 3.7 g (66%). The melting point of the product (recrystallized from methanol) was 94-95° C. The 1H-NMR spectrum (100 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 1.50 (t, J=7.0 Hz, 3H, CH3); 4.02 (q, J=7.0 Hz, 2H, CH2); 6.95-6.39 (m, 5H, Ar); 7.52-7.70 (m, 2H, Ar); 9.83 (s, 1H, CHO).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed at 80° C. for 24 hours
  2. extractionThe product was extracted with chloroform
  3. extractionThe chloroform extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled
  7. customThe product was recrystallized from methanol
  8. customThe melting point of the product (recrystallized from methanol)
  9. customwas 94-95° C

Quellen und Nachweise

ORD-Eintrag
ord-82e2035ccbc6486fafa9479cfcbc429d
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07445877B2

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