1,2-Dibromoethane → ethyl 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([SH:12])[NH:9]2)=[CH:4][C:3]=1[F:19].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH2:27]Br>CN(C)C=O>[CH2:16]([O:15][C:13]([C:7]1[C:6](=[O:18])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([F:19])[CH:4]=2)[N:9]2[CH2:26][CH2:27][S:12][C:8]=12)=[O:14])[CH3:17]Participants
Procedure
Three grams (0.01 mol) of ethyl 7-chloro-6-fluoro-2-mercapto-4-oxo-1,4-dihydroquinoline-3-carboxylate was dissolved in 10 ml of dimethyl formamide, then 4.1 grams (0.03 mol) of anhydrous potassium carbonate was added thereto and, with stirring at a room temperature, 1.9 grams (0.01 mol) of ethylene dibromide was dropped thereinto. The mixture was stirred at a room temperature overnight. The content was concentrated under reduced pressure and water was added to the residue. Crystals separated out therefrom were collected by filtration immediately, washed with water, dried and the crystals were recrystallized from ethanol to give the title compound. Colorless crystals. Yield 3.5 grams (94 percent). All of melting point, elementary analysis data, infrared absorption spectra, and nuclear magnetic resonance spectra coincided with those in example 15.
Workup
- stirringThe mixture was stirred at a room temperature overnight
- concentrationThe content was concentrated under reduced pressure and water
- additionwas added to the residue
- customCrystals separated out
- filtrationtherefrom were collected by filtration immediately
- washwashed with water
- customdried
- customthe crystals were recrystallized from ethanol
Sources & evidence
- ORD record
- ord-5fef51a86c8b49efa64a32eb598a08dd
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04426381
Reaction notes
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