Dimethylformamide → HCID 70268247, compound

HRID 1076067Notes

Reaction equation

HRID 1076067 reaction equation
I[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][S:13]([C:15]1[CH:21]=[CH:20][C:18](N)=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+].C[N:29](C)C=O>[Cu]>[F:8][C:6]1[CH:7]=[C:2]([C:18]2[CH:20]=[CH:21][C:15]([S:13]([CH3:12])=[O:14])=[CH:16][CH:17]=2)[C:3]([N+:9]([O-:11])=[O:10])([NH2:29])[CH2:4][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 114350654-(Methylsulfinyl)anilineHCID 193619484-Fluoro-2-iodo-1-nitrobenzene

Product 1

HCID 70268247HCID 70268247, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

2-Iodo-4-fluoronitrobenzene (0.2 mole) and p-methylsulfinylaniline (0.2 mole) are refluxed in dry dimethylformamide (300 ml.) containing copper powder (5 gm.) and some powdered potassium carbonate (20 gm.) under nitrogen for 18 hours. The solution is filtered and the organics washed with water (6 × 100 ml.) in benzene (600 ml.). The benzene layer is extracted with 2.5 N HCl (7 × 200 ml.) and the acid layer poured onto powdered sodium bicarbonate. The basic solution is extracted with benzene (6 × 200 ml.), the benzene layer washed with water (3 × 100 ml.), separated, dried (MgSO4) and filtered. Evaporation of the solvent followed by chromatography on a 2 in. × 24 in. column of silica-gel (Baker) eluted with various proportions of benzene-hexane mixtures gives pure 5-fluoro-4'-methylsulfinyl-2-nitrobiphenylamine.

Workup

  1. filtrationThe solution is filtered
  2. washthe organics washed with water (6 × 100 ml.) in benzene (600 ml.)
  3. extractionThe benzene layer is extracted with 2.5 N HCl (7 × 200 ml.)
  4. additionthe acid layer poured
  5. extractionThe basic solution is extracted with benzene (6 × 200 ml.)
  6. washthe benzene layer washed with water (3 × 100 ml.)
  7. customseparated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customEvaporation of the solvent
  11. washcolumn of silica-gel (Baker) eluted with various proportions of benzene-hexane

Sources & evidence

ORD record
ord-62cbe5a132d342c498d1153a0e0ead20
Source dataset
uspto-grants-1976_05
Patent number
US03954852

Reaction notes

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