Dimethylformamide → 10-Ethylphenothiazine-3-carbaldehyde

HRID 6578

Reaktionsgleichung

Reaktionsgleichung von HRID 6578
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) 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. Then, 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 with anhydrous sodium sulfate, filtered and distilled. The product was crystallized from methanol. The yield of 10-ethylphenothiazine-3-carbaldehyde (C15H13NOS, FW=255.34) was 65%.

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 with anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled
  7. customThe product was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-aab5b1b567764967a3b9eb9b16000b36
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07083884B2

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