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

HRID 131319

Reaction equation

HRID 131319 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-969fc38ec8ee481694776360b552c66a
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

Loading…