Potassium Chloride → 1,2,4,5-Tetrahydro-4-methyl-1-phenyl-3H-2,4-benzodiazepin-3-thione

HRID 54964

Reaktionsgleichung

Reaktionsgleichung von HRID 54964
Cl.Cl.[CH3:3][NH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:13].C([O-])(=O)C.[K+].[C:25](=S)=[S:26].C(S)(=S)N.[Cl-].[K+]>C(O)(C)C>[CH3:3][N:4]1[C:25](=[S:26])[NH:13][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5]1

Komponenten

7

Edukt 5

HCID 4873Potassium ChlorideHCID 6348Carbon DisulfideHCID 517044Potassium AcetateHCID 3001860Carbamodithioic acidHCID 199570592-[(Methylamino)methyl]-alpha-phenylbenzenemethanamine dihydrochloride

Produkt 1

HCID 149783071,2,4,5-Tetrahydro-4-methyl-1-phenyl-3H-2,4-benzodiazepin-3-thioneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

To a suspension of 15 g (50 mmol) of 2-[(methylamino)methyl]-α-phenylbenzenemethanamine dihydrochoride in 100 mL of isopropyl alcohol was added 10 g (100 mmol) of potassium acetate followed by 3.3 mL (55 mmol) of carbon disulfide in 35 mL of isopropyl alcohol. The suspension was stirred at room temperature for one and one-half hours and then refluxed for 30 minutes. The reaction was chilled in ice and the internal salt of the carbamodithioic acid, contaminated with two equivalents of of potassium chloride, was filtered off. The carbamodithioic acid was suspended in 125 mL of 95% ethanol, and 1.3 mL of of 12N hydrochloric acid was added. The suspension was refluxed for three days, cooled, and 15.3 g (114%) of the crude benzodiazepin-3-thione was filtered off. A 6-g portion of the crude product was recrystallized from 2-ethoxy ethanol to yield 2.0 g (38%) of product, mp 208-209.

Aufarbeitung

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe reaction was chilled in ice
  3. filtrationwas filtered off
  4. addition1.3 mL of of 12N hydrochloric acid was added
  5. temperatureThe suspension was refluxed for three days
  6. temperaturecooled
  7. filtration15.3 g (114%) of the crude benzodiazepin-3-thione was filtered off
  8. customA 6-g portion of the crude product was recrystallized from 2-ethoxy ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2068da37eed34df5b6bdbddc2bfafcbc
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624922

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