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 1418943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1418943
[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,11 H-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-d9ac3941149a45f1bd3848a87ba751c6
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05885986

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