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

HRID 131319

Reaktionsgleichung

Reaktionsgleichung von HRID 131319
[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 title 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-969fc38ec8ee481694776360b552c66a
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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