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

HRID 131326Notes

Reaction equation

HRID 131326 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 this a solution of tin (II) chloride (29.1 g, 153.67 mmol) in 5.0 N hydrochloric acid (170 ml). Heat the resulting mixture to reflux for 18 hours. Cool the reaction to room temperature and place in a freezer for 24 hours. Precipitate the product from the solution and collect by filtration to btain 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 the resulting mixture
  2. temperatureto reflux for 18 hours
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationPrecipitate the product from the solution and collect by filtration

Sources & evidence

ORD record
ord-44697ed61f674560914c755a20efde48
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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