Hydrochloric Acid → N-(4-Oxo-3,4-dihydro-2H-chromen-6-yl)benzenesulfonamide

HRID 493141Notes

Reaction equation

HRID 493141 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12].N1C=CC=CC=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C(Cl)Cl>[O:12]=[C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][S:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:27])=[O:26])[CH:3]=2)[O:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 200709836-Amino-2,3-dihydro-4H-1-benzopyran-4-one

Product 1

HCID 69057035N-(4-Oxo-3,4-dihydro-2H-chromen-6-yl)benzenesulfonamideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-amino-2,3-dihydro-4H-chromen-4-one (330 mg, 2.02 mmol) in CH2Cl2 is treated with pyridine (1 mL) and benzenesulfonyl chloride (0.28 mL, 2.2 mmol), stirred at ambient temperature for 1 hour, poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic phase is washed sequentially with dilute hydrochloric acid until the pH of the wash is <2 and a saturated solution of sodium bicarbonate, dried over MgSO4 and concentrated in vacuo to afford the title compound as a beige solid, 460 mg (74% yield), identified by NMR and mass spectral analyses.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed sequentially with dilute hydrochloric acid until the pH of the wash
  3. dry with materiala saturated solution of sodium bicarbonate, dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44eace2b13104f53b8fdc25836c2f921
Source dataset
uspto-grants-2009_05
Patent number
US07534801B2

Reaction notes

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