Dimethylformamide → 10-Ethylphenothiazine-3-carbaldehyde

HRID 1375308

反応式

HRID 1375308 の反応式
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

5

反応物 4

HCID 6228Dimethylformamide2 回HCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 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).

後処理

  1. temperatureThe reaction mixture was heated 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 recrystallized from methanol
  8. customa melting point of 94–95° C. (recrystallized from methanol)
  9. customA 1H NMR spectrum yielded the
  10. customfollowing results

出典と根拠

ORDレコード
ord-47241199647d4ce089373cf99779e30a
出典データセット
uspto-grants-2007_01
特許番号
US07169520B2

関連ノート

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