Ethanethiol → HCID 13565847, compound

HRID 1589562Notes

Reaction equation

HRID 1589562 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](Cl)[N:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[K+].[CH2:22]([SH:24])[CH3:23]>CN(C)C=O.C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([S:24][CH2:22][CH3:23])[N:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 14797Potassium HydroxideHCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 13565847HCID 13565847, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3.40 g (12 mmol) 1-cyclopropyl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid in 60 ml N,N-dimethylformamide heated to 60° C. was treated with a solution of 3.36 g (60 mmol) potassium hydroxide and 6 ml (81 mmol) ethanethiol in 30 ml absolute ethanol. After stirring 15 minutes at 60° C. the mixture was poured into 240 ml ice cold 0.5 N hydrochloric acid, and the precipitate was filtered, washed with water and crystallized from acetic acid--water to give 3.10 g, mp 242°-244° C. of the title compound.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customcrystallized from acetic acid

Sources & evidence

ORD record
ord-23d6f72dba7f47a793c66fe1e102f8a4
Source dataset
uspto-grants-1986_02
Patent number
US04571396

Reaction notes

Loading…