Water → 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepine-6-thione

HRID 1046990

Reaktionsgleichung

[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=O)[NH:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1.O>N1C=CC=CC=1>[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=[S:26])[NH:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (3.00 g, 14 mmol) and Lawesson's reagent (6.51 g, 16 mmol) in pyridine (40 mL) was heated to 100° C. for 18 hours. After cooling to room temperature the mixture was poured into water and stirred. The precipitate was collected on a filter paper and dried. The crude product (yellow solid) was carried on to the next step without further purification (96%). 1H NMR (DMSO-d6) 400 MHz δ: 11.99 (s, 1H), 8.37, (s, 1H), 7.98 (dd, J=4.6, 1.7 Hz, 1H), 7.96 (dd, J=8.0, 1.7 Hz, 1H), 7.44 (dd, J=7.7, 1.4 Hz, 1H), 7.35 (td, J=7.7, 1.7 Hz, 1H), 7.06 (dd, J=8.0, 1.2 Hz, 1H), 7.01 (dd, J=8.0, 4.6 Hz, 1H), 6.95 (td, J=8.0, 1.2 Hz, 1H); LC/MS [M+H]: 228.

Aufarbeitung

temperatureAfter cooling to room temperature the mixture
customThe precipitate was collected on a filter paper
customdried
customThe crude product (yellow solid) was carried on to the next step without further purification (96%)

Quellen und Nachweise

ORD-Eintrag: ord-448bfb118ec4408182701b8f1450fcf7
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08569331B2

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