Hydrochloric Acid → 9-(2-Dimethylamino-1-methylethyl)-4,9-dihydro-4-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one, hydrochloride

HRID 1606442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1606442
[H-].[Na+].Cl.[CH3:4][N:5]([CH3:10])[CH2:6][CH:7]([Cl:9])[CH3:8].[CH3:11][N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][C:15](=[O:23])[C:14]2=[CH:24][S:25][CH:26]=[C:13]12.Cl>C(O)C.CCOCC.CN(C)C=O>[ClH:9].[CH3:4][N:5]([CH3:10])[CH2:6][CH:7]([N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:12]([CH3:11])[C:13]2=[CH:26][S:25][CH:24]=[C:14]2[C:15]1=[O:23])[CH3:8]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 942942-Chloropropyldimethylamine hydrochlorideHCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Produkt 1

HCID 1317101509-(2-Dimethylamino-1-methylethyl)-4,9-dihydro-4-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one, hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.47 g. of 55% sodium hydride-mineral oil dispersion and 0.83 g. of 2-dimethylamino-1-methylethylchloride hydrochloride in 30 ml. of dry dimethylformamide is stirred at room temperature for 0.5 hours. To the mixture is added 0.6 g. of 4,9-dihydro-4-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one and stirring is continued for 18 hours. The reaction mixture is cooled, quenched with water and extracted with chloroform. The dried chloroform extracts are concentrated to an oil which is chromatographed on silica gel preparative thin layer chromatographic (tlc) plates using 10:1 benzene:methanol to give a yellow oil. The oil is dissolved in ethanol and treated with anhydrous hydrogen chloride followed by dilution with ether to give a solid, which is recrystallized from ethanol to give white crystals, m.p. 280°-282°C. (dec.).

Aufarbeitung

  1. additionA mixture of 0.47 g
  2. additionTo the mixture is added 0.6 g
  3. temperatureThe reaction mixture is cooled
  4. customquenched with water
  5. extractionextracted with chloroform
  6. concentrationThe dried chloroform extracts are concentrated to an oil which
  7. customis chromatographed on silica gel preparative thin layer chromatographic (tlc) plates
  8. custommethanol to give a yellow oil
  9. customto give a solid, which
  10. customis recrystallized from ethanol
  11. customto give white crystals, m.p. 280°-282°C. (dec.)

Quellen und Nachweise

ORD-Eintrag
ord-e64d51aee9384b33bf300a123532547a
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03953430

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