Acetone → HCID 14839595, compound

HRID 1089224Notes

Reaction equation

HRID 1089224 reaction equation
CC(C)=O.[CH2:5]([O:7][C:8]([C:10]1[C:19](=[O:20])[C:18]2[C:13](=[N:14][C:15](Cl)=[C:16]([F:21])[CH:17]=2)[N:12]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:11]=1)=[O:9])[CH3:6].C(=O)([O-])[O-].[K+].[K+].[CH2:33]([SH:35])[CH3:34]>O.C(OC(=O)C)C>[CH2:5]([O:7][C:8]([C:10]1[C:19](=[O:20])[C:18]2[C:13](=[N:14][C:15]([S:35][CH2:33][CH3:34])=[C:16]([F:21])[CH:17]=2)[N:12]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:11]=1)=[O:9])[CH3:6]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 11844477HCID 11844477, compound

Product 1

HCID 14839595HCID 14839595, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetone (90 mL) was added to a mixture of 1.96 g (6 mmoles) of 6-fluoro-7-chloro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8 naphthyridine-3-carboxylic acid ethyl ester and 2.5 g (18 mmoles) of anhydrous potassium carbonate. To this suspension was added 1.33 mL (18 mmoles) of ethanethiol. After heating to reflux for 2.5 hours, the solvent was eliminated in vacuo. The residue was taken up with ethylacetate and water. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. The resulting solid was treated with ether to give 1.67 g of titled compound. MP 159°-60° C.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 2.5 hours
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. additionThe resulting solid was treated with ether

Sources & evidence

ORD record
ord-e59b5ca5352346efba2fb8d784362539
Source dataset
uspto-grants-1990_10
Patent number
US04965273

Reaction notes

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