Thionyl Chloride → 3-Dichloromethylthio-7-fluoro-1-methyl-4-quinolone

HRID 2181774Notes

Reaction equation

HRID 2181774 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][CH2:6][S:7]([C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([F:20])=[CH:15][CH:16]=2)[N:11]([CH3:21])[CH:10]=1)=O>N1C=CC=CC=1>[Cl:5][CH:6]([Cl:3])[S:7][C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([F:20])=[CH:15][CH:16]=2)[N:11]([CH3:21])[CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 104685473-Chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone2×

Product 1

HCID 113237793-Dichloromethylthio-7-fluoro-1-methyl-4-quinolone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an efficiently stirred and gently cooled 4.2 ml mixture of thionyl chloride (“SOCl2”) and 1.05 ml of pyridine (“Py”) at −3° C. was added 1.015 g (3.708 mmol) of 3-chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone (monochloroflosequinan) (Compound 1 of FIG. 1). This addition was made in multiple alloquots over a period of approximately 1 min. During this addition, cooling was applied to keep the temperature in the range 0-5° C.

Workup

  1. additionThis addition
  2. additionDuring this addition
  3. temperaturecooling
  4. customin the range 0-5° C.

Sources & evidence

ORD record
ord-45a8f65e14a94100ac1826e7d5c685a6
Source dataset
uspto-grants-2005_05
Patent number
US06894166B2

Reaction notes

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