Benzenesulfonyl chloride → HCID 18617325, compound

HRID 842890Notes

Reaction equation

HRID 842890 reaction equation
[NH2:1][C:2]1[C:6]([Br:7])=[C:5]([CH3:8])[O:4][N:3]=1.[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1.ClCCl>[C:9]1([S:15]([N:1]([C:2]2[C:6]([Br:7])=[C:5]([CH3:8])[O:4][N:3]=2)[S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 27744644-Bromo-5-methyl-1,2-oxazol-3-amine

Product 1

HCID 18617325HCID 18617325, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

3-Amino-4-bromo-5-methylisoxazole (5.31 g, 30 mmol) was dissolved in dry pyridine (30 ml). Benzenesulfonyl chloride (5.24 ml, 42 mmol) was added dropwise with stirring at ambient temperature. N,N-(Dimethyl)aminopyridine (100 mg) was added and stirring was continued at 50° C. for 25 h. The reaction mixture was diluted with dichloromethane (200 ml), washed with 1N HCl (6×100 ml) and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product which was purified by column chromatography using 9:1, hexanes/ethyl acetate as eluent to give N-(benzenesulfonyl)-N-(4-bromo-5-methyl-3-isoxazolyl)benzenesulfonamide (7 g, 51% yield, Rf=0.27 using 3:1, hexanes/ethyl acetate as eluent) as a solid.

Workup

  1. stirringstirring
  2. washwashed with 1N HCl (6×100 ml)
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto yield a crude product which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ce8d838324bb431993ceb288e6c9073c
Source dataset
uspto-grants-2002_04
Patent number
US06376523B1

Reaction notes

Loading…