Stannous Chloride → HCID 86604574, compound

HRID 131336Notes

Reaction equation

HRID 131336 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][C:10]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:11]=2[C:12]#[N:13])=[C:4]([N+:22]([O-])=O)[CH:3]=1.[Sn](Cl)[Cl:26]>C(O)C.Cl>[ClH:26].[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]2[N:22]=[C:12]([NH2:13])[C:11]3[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:10]=3[NH:9][C:5]=2[CH:6]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 586259642-(4,5-Difluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile

Product 1

HCID 86604574HCID 86604574, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent

Procedure

Heat a solution of 2-(4,5-difluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile (0.995 g, 2.90 mmol) in ethanol (15 ml) to 60° C. Add to this a solution of tin (II) chloride (1.65 g, 8.70 mmol) in 5.0 N hydrochloric acid (15 ml). Heat the resulting mixture to reflux for 18 hours. Cool the reaction to room temperature, add 30 ml of 5.0 N hydrochloric acid and place the mixture in a freezer for 16 hours. Collect by filtration the precipitated product from the solution. Wash solid with 5.0 N hydrochloric acid to obtain 0.648 g of the title compound (1.85 mmol, 64% yield) as a yellow amorphous solid: Mass Spectrum (m/e): 314(M+1).

Workup

  1. temperatureHeat the resulting mixture
  2. temperatureto reflux for 18 hours
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationCollect by filtration the precipitated product from the solution
  6. washWash solid with 5.0 N hydrochloric acid

Sources & evidence

ORD record
ord-ceab243ffb7848e0be70fa6cf9780c89
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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