Hydrogen Sulfide → (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-thiocarboxamide

HRID 1737359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1737359
[SH2:1].[Cl:2][C:3]1[C:8]2[C:9](=[O:21])[N:10]3[CH2:20][CH2:19][C@H:11]3[C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17]#[N:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1>N1C=CC=CC=1.C(N(CC)CC)C>[Cl:2][C:3]1[C:8]2[C:9](=[O:21])[N:10]3[CH2:20][CH2:19][C@H:11]3[C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17](=[S:1])[NH2:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 402Hydrogen SulfideHCID 53905765(S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile

Produkt 1

HCID 86753957(S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-thiocarboxamideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A stream of hydrogen sulphide was conducted for 1 hr. through a solution of 11.3 g (0.0396 mol) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile in 230 ml of pyridine and 2.3 ml of triethylamine. The green solution was left to stand for 48 hrs., then de-gassed with a stream of nitrogen and subsequently completely freed from the solvents. The residue was partitioned between dichloromethane and water and extracted. The pale yellow product was recrystallized in tetrahydrofuran and subsequently in methanol. There were obtained 4.44 g (35%) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-thiocarboxamide as pale yellow crystals; m.p. 250-253° and [α]D20 =-330.6° (DMF, c=1%).

Aufarbeitung

  1. waitThe green solution was left
  2. custom, then de-gassed with a stream of nitrogen
  3. customThe residue was partitioned between dichloromethane and water
  4. extractionextracted
  5. customThe pale yellow product was recrystallized in tetrahydrofuran and subsequently in methanol

Quellen und Nachweise

ORD-Eintrag
ord-ad1704dd96c44649acb50b8090db0c8c
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962450

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