Benzimidazole → 1-[(3,4-Dihydro-2H(1,3)-thiazino[3,2-a]benzimidazole-2-yl)methyl]-4-(3,4,5-trimethoxycinnamoyl)piperazine

HRID 1164399

Reaktionsgleichung

Reaktionsgleichung von HRID 1164399
[N:1]1([CH2:7][CH:8]2NCC=[CH:10][S:9]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][CH:15]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[CH:28]=[CH:29][C:30](Cl)=[O:31].[CH2:40](N(CC)CC)C>C(Cl)(Cl)Cl.O>[S:9]1[C:10]2=[N:14][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]2[CH2:15][CH2:40][CH:8]1[CH2:7][N:1]1[CH2:2][CH2:3][N:4]([C:30](=[O:31])[CH:29]=[CH:28][C:27]2[CH:26]=[C:25]([O:24][CH3:23])[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=2)[CH2:5][CH2:6]1

Komponenten

7

Edukt 4

HCID 5798BenzimidazoleHCID 8471TriethylamineHCID 1120942-Propenoyl chloride, 3-(3,4,5-trimethoxyphenyl)-, (2E)-HCID 1317129353,4-dihydro-2-piperazinomethyl-2H-(1,3)-thiazine

Produkt 1

HCID 540543361-[(3,4-Dihydro-2H(1,3)-thiazino[3,2-a]benzimidazole-2-yl)methyl]-4-(3,4,5-trimethoxycinnamoyl)piperazineAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To 20 ml of chloroform was dissolved 1.0 g (3.5 m mole) of 3,4-dihydro-2-piperazinomethyl-2H-(1,3)-thiazine[3,2-a[benzimidazole, followed by the dropwise addition of 1 g of 3,4,5-trimethoxycinnamoyl chloride in 10 ml of chloroform under ice-cooled stirring conditions. After ten minutes, 0.5 ml of triethylamine was added. The mixture was stirred for 3 hours at room temperature. After the completion of the reaction, the reaction mixture was added with water and extracted with chloroform. The chloroform layer was washed with water and then dried over anhydrous magnesium sulfate. Chloroform was evaporated under reduced pressure and the residue was chromatographed on silica gel and eluted with chloroform to obtain 1.2 g (Yield: 69.4%) of the intended product, m.p. 211°-212° C.;

Aufarbeitung

  1. temperaturecooled
  2. waitAfter ten minutes
  3. stirringThe mixture was stirred for 3 hours at room temperature
  4. customAfter the completion of the reaction
  5. extractionextracted with chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customChloroform was evaporated under reduced pressure
  9. customthe residue was chromatographed on silica gel
  10. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-b80d2e60805f4767962bc8e229809c0e
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04369309

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