Stannous Chloride → 8-Fluoro-2-trifluoromethyl-5h-dibenzo[b,e][1,4]diazepin-11-ylaminehydrochloride

HRID 1350533Notes

Reaction equation

HRID 1350533 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:10]=2[C:11]#[N:12])=[C:4]([N+:21]([O-])=O)[CH:3]=1.[Sn](Cl)[Cl:25]>C(O)C.Cl>[ClH:25].[F:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:10]=3[C:11]([NH2:12])=[N:21][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 210934612-(4-Fluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile

Product 1

HCID 1357977638-Fluoro-2-trifluoromethyl-5h-dibenzo[b,e][1,4]diazepin-11-ylaminehydrochlorideYield 22.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Heat a solution of 2-(4-fluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile (9.995 g, 30.73 mmol) in ethanol (170 ml) to 60° C. Add to a solution of tin (II) chloride (29.1 g, 153.67 mmol) in 5.0 N hydrochloric acid (170 ml) and heat to reflux. After 18 hours, cool the reaction to room temperature and place in a freezer for 24 hours. The product precipitates from the solution and is collected by filtration. Obtained 2.253 g of the title compound (6.79 mmol, 22% yield) as a yellow amorphous solid: Mass Spectrum (m/e): 296(M+1).

Workup

  1. temperatureheat to reflux
  2. temperaturecool
  3. customthe reaction to room temperature
  4. waitplace in a freezer for 24 hours
  5. customThe product precipitates from the solution
  6. filtrationis collected by filtration

Sources & evidence

ORD record
ord-93f7e6732519411fa1b78d59a0302447
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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