Dimethylformamide → HCID 70268247, compound

HRID 376447Notes

Reaction equation

HRID 376447 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 4-methylsulfinylaniline (0.2 mole) are refluxed in dry dimethylformamide (300 ml.) containing copper powder (5 g) and some powdered potassium carbonate (20 g) under nitrogen for 18 hours. The suspension is filtered, and the organics are washed with water (6 times 100 ml.) in benzene (600 ml.). The benzene layer is extracted with 2.5 N HCl (7×200 ml.), and the acid layer is poured onto powdered sodium bicarbonate. The basic solution is extracted with benzene (6 times 200 ml.), the benzene layer is washed with water (3 times 100 ml.), is 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 suspension is filtered
  2. washthe organics are washed with water (6 times 100 ml.) in benzene (600 ml.)
  3. extractionThe benzene layer is extracted with 2.5 N HCl (7×200 ml.)
  4. additionthe acid layer is poured
  5. extractionThe basic solution is extracted with benzene (6 times 200 ml.)
  6. washthe benzene layer is washed with water (3 times 100 ml.)
  7. customis separated
  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 mixtures

Sources & evidence

ORD record
ord-98c05c07ecd1415c978b12d700d55e8d
Source dataset
uspto-grants-2000_02
Patent number
US06020379

Reaction notes

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