Dimethylformamide → 10-Ethylphenothiazine-3-carbaldehyde

反応式

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]

参加物

反応物 4

HCID 6228Dimethylformamide2 回

HCID 14797Potassium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 219178N-Ethylphenothiazine

生成物 1

HCID 31433010-Ethylphenothiazine-3-carbaldehyde

実験手順

A 3.7 ml (0.04 mol) quantity of phosphorus oxychloride (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. Then 5 g (0.02 mol) of 10-ethylphenothiazine in dry DMF was added dropwise to the solution. The reaction mixture was heated at 80° C. for 24 hours and poured into ice water. The obtained 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 recrystallized from methanol. The yield of 10-ethylphenothiazine-3-carbaldehyde was 3.7 g (66%). The product had a melting point of 94–95° C. (recrystallized from methanol). A 1H NMR spectrum yielded the following results: (100 MHz, CDCl3, 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).