Thionyl Chloride → N-(2-Benzoylphenyl)-4-(2-oxopyrrolidin-1-yl)benzene-1-sulfonamide

HRID 746748Notes

Reaction equation

HRID 746748 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([OH:7])=O.S(Cl)(Cl)=O.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1>CN(P(N(C)C)(N(C)C)=O)C.C(#N)C>[C:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([N:12]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:7])=[CH:14][CH:15]=1)(=[O:21])=[O:20])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 758094-Bromobutyric acidHCID 693089944-Amino-N-(2-benzoylphenyl)benzene-1-sulfonamide

Product 1

HCID 58664932N-(2-Benzoylphenyl)-4-(2-oxopyrrolidin-1-yl)benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 20373099HCID 20373099, compoundSolvent

Procedure

A solution of 474 mg (2.84 mmol) of 4-bromo-butanoic acid in 6 mL of 5:1 HMPA/acetonitrile was cooled to 0 deg and thionyl chloride (0.207 mL, 2.84 mmol) was added. The reaction mixture was warmed to room temperature, and transferred to a flask containing 250 mg (0.709 mmol) of neat 4-amino-N-(2-benzoylphenyl)benzenesulfonamide. The solution was allowed to stir overnight. The reaction was quenched w/saturated sodium bicarbonate and diluted with EtOAc (˜100 mL), washed with water (3×20 mL) and brine (1×20 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via flash chromatography (15% to 75% EtOAc/hexanes)to provide the title compound. LC/MS (ES MS, M+H+ found: 457).

Workup

  1. customtransferred to a flask
  2. customThe reaction was quenched w/saturated sodium bicarbonate
  3. additiondiluted with EtOAc (˜100 mL)
  4. washwashed with water (3×20 mL) and brine (1×20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via flash chromatography (15% to 75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a77776605ad14b689a350caad336b178
Source dataset
uspto-grants-2008_07
Patent number
US07393873B2

Reaction notes

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