Sodium Thiosulfate → HCID 86654251, compound

HRID 590925Notes

Reaction equation

HRID 590925 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[C:3]=1[NH:22][C:23](=[O:33])[C:24]1[CH:29]=[CH:28][C:27](I)=[C:26]([NH:31][CH3:32])[CH:25]=1.[Cu][C:35]#[N:36].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[C:3]=1[NH:22][C:23](=[O:33])[C:24]1[CH:29]=[CH:28][C:27]([C:35]#[N:36])=[C:26]([NH:31][CH3:32])[CH:25]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 86654252HCID 86654252, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86654251HCID 86654251, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To 10 mL of DMF were added 0.350 g (0.560 mmol) of N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-iodo-3-(methylamino)benzamide and 0.200 g (2.25 mmol) of copper (I) cyanide, followed by stirring at 140° C. for 1 hour and 30 minutes. A saturated aqueous sodium thiosulfate solution was poured into the reaction solution to quench the reaction, and the organic layer was collected with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=5:1→3:1) to prepare 0.250 g (yield 86%) of a target compound.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe organic layer was collected with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=5:1→3:1)

Sources & evidence

ORD record
ord-529d2d9ef52e4457bf73b752e394eddc
Source dataset
uspto-grants-2016_01
Patent number
US09237745B2

Reaction notes

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