Aniline → HCID 8190068, compound

HRID 226172Notes

Reaction equation

HRID 226172 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) (110 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-cbab79098f9343f3ad04fa8eb18a1deb
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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