Aniline → HCID 8190068, compound

HRID 351078Notes

Reaction equation

HRID 351078 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 10340Sodium CarbonateHCID 17943m-Bromobenzenesulphonyl chloride

Product 1

HCID 8190068HCID 8190068, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

3-Bromobenzenesulfonyl chloride (51a) (1.0 g, 3.9 mmol) was added to a mixture of aniline (0.47 g, 5.1 mmol) in acetonitrile (10 ml) and sodium carbonate (1.3 g, 12.3 mmol) in water (10 ml). The mixture was stirred at ambient temperature for 1 hour and the reaction product was extracted with ethyl acetate (30 ml). The extract was dried (Na2SO4) and solvents were removed under reduced pressure to give the title compound (1.15 g, 94%) as an oil witch solidified upon standing. M.p. 98–100° C. 1H NMR (DMSO-d6, HMDSO) δ: 6.94–7.48 (5H, m, C6H5); 7.50–7.96 (4H, m, C6H4); 10.36 (1H, s, NH).

Workup

  1. extractionthe reaction product was extracted with ethyl acetate (30 ml)
  2. dry with materialThe extract was dried (Na2SO4) and solvents
  3. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-3e70b27bbd2244c3aa70b5d2b227bfdb
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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