Dimethylformamide → 10-Ethylphenothiazine-3-carbaldehyde

반응식

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]

참가 물질

반응물 4

HCID 6228Dimethylformamide2회

HCID 14797Potassium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 219178N-Ethylphenothiazine

생성물 1

HCID 31433010-Ethylphenothiazine-3-carbaldehyde

실험 절차

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%.