N-Acetylsulfanilyl chloride → HCID 18918200, compound

HRID 1290731Notes

Reaction equation

HRID 1290731 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:20])=[C:10]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:11]=2[F:13])[C:6](=[O:21])[C:5]([C:22]([OH:24])=[O:23])=[CH:4]1)[CH3:2].[C:25]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)(=[O:27])[CH3:26]>N1C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:20])=[C:10]([N:14]3[CH2:15][CH2:16][N:17]([S:35]([C:32]4[CH:31]=[CH:30][C:29]([NH:28][C:25](=[O:27])[CH3:26])=[CH:34][CH:33]=4)(=[O:37])=[O:36])[CH2:18][CH2:19]3)[C:11]=2[F:13])[C:6](=[O:21])[C:5]([C:22]([OH:24])=[O:23])=[CH:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 1135233-Quinolinecarboxylic acid, 1,4-dihydro-6,8-difluoro-1-ethyl-4-oxo-7-(1-piperazinyl)-

Product 1

HCID 18918200HCID 18918200, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

2.80 g of 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid is suspended in 100 ml of pyridine. To this suspension is slowly added 7.76 g of 4-acetamidobenzenesulfonyl chloride in 20 ml of benzene under ice-cooling while stirring. Stirring is continued for 1 hour under ice-cooling and then for further 3 hours at room temperature. The reaction mixture is concentrated under reduced pressure. To the residue is added 1N sodium hydroxide solution to dissolve. The pH of the solution is then adjusted to 4 with acetic acid. Precipitating crystals are collected by filtration, washed with water and recrystallized from dimethylformamide (DMF)-ethanol to give 4.10 g of the titled compound. Melting point: 276°-277° C.

Workup

  1. temperaturecooling
  2. stirringStirring
  3. temperaturecooling
  4. waitfor further 3 hours at room temperature
  5. concentrationThe reaction mixture is concentrated under reduced pressure
  6. additionTo the residue is added 1N sodium hydroxide solution
  7. dissolutionto dissolve
  8. customPrecipitating crystals
  9. filtrationare collected by filtration
  10. washwashed with water
  11. customrecrystallized from dimethylformamide (DMF)-ethanol

Sources & evidence

ORD record
ord-5f868b0b3d1e4eb4a6837624acfb27d8
Source dataset
uspto-grants-1998_05
Patent number
US05753658

Reaction notes

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