Stannous Chloride → 2-Trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

HRID 1350531

Reaktionsgleichung

Reaktionsgleichung von HRID 1350531
[Sn](Cl)[Cl:2].[N+:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:15]=1[C:16]#[N:17])([O-])=O>Cl.C(O)C>[ClH:2].[F:23][C:22]([F:25])([F:24])[C:19]1[CH:20]=[CH:21][C:14]2[NH:13][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:4]=[C:16]([NH2:17])[C:15]=2[CH:18]=1

Komponenten

5

Edukt 2

HCID 24479Stannous ChlorideHCID 210934552-(2-Nitro-phenylamino)-5-trifluoromethyl-benzonitrile

Produkt 1

HCID 210935172-Trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

Add a solution of tin(II) chloride (567 mg, 3 mmol) in 12 N hydrochloric acid (1.8 mL) to a solution of 2-(2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile (307 mg, 1 mmol) in ethanol (10 mL). Reflux for 24 hours, then concentrate under vacuum, add water and filter. Wash the resulting solid with water and dichloromethane then dry under vaccum to yield the titled compound as a yellow solid (282 mg, 90%): mp 334–336° C.; 1H NMR (DMSO-d6) δ 7.05–7.19 (m, 4H), 7.34 (d, 1H), 7.86 (dd, 1H), 7.87 (s, 1H), 8.79 (s, 1H), 9.26 (s, 1H), 9.75 (s, 1H), 12.40 (s, 1H). MS (ESI/neg) m/z (rel intensity) 276.1 (100).

Aufarbeitung

  1. temperatureReflux for 24 hours
  2. concentrationconcentrate under vacuum
  3. additionadd water
  4. filtrationfilter
  5. washWash the resulting solid with water and dichloromethane
  6. customthen dry under vaccum

Quellen und Nachweise

ORD-Eintrag
ord-f29372896b9a49f4b6e4a2b1cdafa4df
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214673B2

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