Triethylamine → HCID 11793560, compound

HRID 439394Notes

Reaction equation

HRID 439394 reaction equation
[Br:1]N1C(=O)CCC1=O.C(N(CC)CC)C.[F:16][C:17]([F:34])([F:33])[C:18]1[CH:22]=[C:21]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[O:20][N:19]=1>C(Cl)(Cl)Cl>[Br:1][C:22]1[C:18]([C:17]([F:16])([F:33])[F:34])=[N:19][O:20][C:21]=1[NH:23][S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 10708746HCID 10708746, compound

Product 1

HCID 11793560HCID 11793560, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-Bromosuccinimide (64 mg, 0.35 mmol) and triethylamine (0.072 ml, 0.51 mmol) were added to a solution of N-(3-trifluoromethyl-5isoxazolyl)benzenesulfonamide(100 mg, 0.34 mmol)in chloroform (20 ml) at room temperature. The reaction was stirred at room temperature for 2 h. Chloroform (30 ml) was added and the solution was washed with 1N hydrochloric acid (40 ml), dried over magnesium sulfate and concentrated. The crude product was purified by HPLC to afford 114 mg (90%) N-(4-bromo-3-trifiuoromethyl-5-isoxazolyl)benzenesulfonamide as an off-white solid, m.p. 104°-105° C.

Workup

  1. washthe solution was washed with 1N hydrochloric acid (40 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-694499b7624a47e6b3e33fb0efa38793
Source dataset
uspto-grants-1996_05
Patent number
US05514691

Reaction notes

Loading…