Dimethylformamide → 10-Ethylphenothiazine-3-carbaldehyde

HRID 268577

反応式

HRID 268577 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

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).

後処理

  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

出典と根拠

ORDレコード
ord-82e2035ccbc6486fafa9479cfcbc429d
出典データセット
uspto-grants-2008_11
特許番号
US07445877B2

関連ノート

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