Stannous Chloride → 6-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

HRID 131307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131307
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([NH:8][C:9]2[S:10][C:11]([CH3:16])=[CH:12][C:13]=2[C:14]#[N:15])[CH:7]=1.[Sn](Cl)Cl>C(O)C.Cl.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:17]=[C:14]([NH2:15])[C:13]3[CH:12]=[C:11]([CH3:16])[S:10][C:9]=3[NH:8][C:6]=2[CH:7]=1

Komponenten

6

Edukt 2

HCID 24479Stannous ChlorideHCID 586260242-(5-Chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile

Produkt 1

HCID 692144886-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochlorideAusbeute 180,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Suspend 2-(5-chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile (0.58 g, 1.98 mmol) in ethanol (20 ml), add anhydrous tin(II)chloride(1.5 g, 6.66 mmol) in concentrated hydrochloric acid (6 ml) and heat the mixture under reflux for 75 minutes. Dilute the mixture with water and allow to cool. Collect the precipitate by filtration and dry under high vacuum to give 6-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride as a yellow solid (0.537 g, 90%): Mass Spectrum (FIA) 300/302 (M+1).

Aufarbeitung

  1. temperatureheat the mixture
  2. temperatureunder reflux for 75 minutes
  3. temperatureto cool
  4. customCollect the precipitate
  5. filtrationby filtration
  6. customdry under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4dae3d9cbde84c11a3e4208cc091ae2d
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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