4-Chlorobutyryl chloride → HCID 19066387, compound

HRID 481386Notes

Reaction equation

HRID 481386 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:17]=2)[C:12](=[O:28])[C:11]([CH3:30])([CH3:29])[CH2:10]1>N1C=CC=CC=1>[CH3:29][C:11]1([CH3:30])[C:12](=[O:28])[C:13]2[C:18](=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:9]([N:8]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[CH2:10]1

Participants

4

Reactant 2

HCID 783704-Chlorobutyryl chlorideHCID 19066390HCID 19066390, compound

Product 1

HCID 19066387HCID 19066387, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

While stirring under chilling with ice water, 220 μl of chlorobutyryl chloride were added to a solution of 550 mg of 1-amino-2,3-dihydro-3,3-dimethyl-7-phenylsulfonyl-4(1H)-quinolinone in pyridine. After stirring overnight at room temperature, the liquid reaction mixture was extracted with chloroform with the system acidified with hydrochloric acid. After the extract was dried over magnesium sulfate, chloroform was distilled off. The residue was dissolved in dimethylformamide, and 91 mg of sodium hydride were added to the solution under chilling with ice water to stir the resultant mixture at room temperature for 30 minutes. After completion of the reaction, ice water was added to the liquid reaction mixture, which was then extracted with diethyl ether. After the extract was dried over magnesium sulfate, diethyl ether was distilled off, and the residue was purified by column chromatography on silica gel to obtain 249 mg (yield: 41%) of the title compound as yellow crystals.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. customthe liquid reaction mixture
  3. extractionwas extracted with chloroform with the system
  4. dry with materialAfter the extract was dried over magnesium sulfate, chloroform
  5. distillationwas distilled off
  6. dissolutionThe residue was dissolved in dimethylformamide
  7. addition91 mg of sodium hydride were added to the solution
  8. temperatureunder chilling with ice water
  9. stirringto stir the resultant mixture at room temperature for 30 minutes
  10. customAfter completion of the reaction, ice water
  11. additionwas added to the liquid reaction mixture, which
  12. extractionwas then extracted with diethyl ether
  13. dry with materialAfter the extract was dried over magnesium sulfate, diethyl ether
  14. distillationwas distilled off
  15. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ce9b2be61bfa4638b0498bca99a4c664
Source dataset
uspto-grants-1998_08
Patent number
US05789419

Reaction notes

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