Benzenesulfonyl chloride → 4-(Benzenesulfonyl)-1,3-dihydroquinoxalin-2-one

HRID 2165526

Reaction equation

HRID 2165526 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][C:2]1=[O:11].C(=O)([O-])[O-].[K+].[K+].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[C:18]1([S:24]([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:1][C:2](=[O:11])[CH2:3]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-

Product 1

HCID 10932374-(Benzenesulfonyl)-1,3-dihydroquinoxalin-2-oneYield 52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 10 g. (0.068 mole) of 3,4-dihydro-2(1H)-quinoxalinone (3,4-dihydro-2-hydroxyquinoxaline) [prepared in 50% yield according to the procedure described by W. H. Perkin et al. in the Journal of the Chemical Society, Vol. 123, p.2399(1923)] and 9.6 g. (0.069 mole) of potassium carbonate in 250 ml. of acetone was stirred under a nitrogen atmosphere at 40° C., while 11.5 g. (0.07 mole) of benzenesulfonyl chloride was added during the course of a 30-minute period. The reaction mixture was next heated at reflux temperature for 14 hours and then poured onto 500 ml. of ice. The resulting brown solid was recrystallized from ethyl acetate to yield 10.2 g (52%) of pure 4-benzenesulfonyl-3,4-dihydro-2(1H)-quinoxalinone, m.p. 183°-185° C. The pure product was further characterized by means of nuclear magnetic resonance data and elemental analysis.

Workup

  1. additionA suspension of 10 g
  2. temperatureThe reaction mixture was next heated
  3. temperatureat reflux temperature for 14 hours
  4. additionpoured onto 500 ml
  5. customThe resulting brown solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e63bd5bf0967443388cb193dc309b8b9
Source dataset
uspto-grants-1990_07
Patent number
US04940708

Linked notes

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