Sulfuryl chloride → HCID 59292845, compound

HRID 2409776Notes

Reaction equation

HRID 2409776 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH2:6]([O:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[C:22]=2[F:31])=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2)=[O:10])[CH3:7]>CC#N>[CH2:6]([O:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:21]2[C:22]([F:31])=[C:23]([O:29][CH3:30])[CH:24]=[C:25]([O:27][CH3:28])[C:26]=2[Cl:4])=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2)=[O:10])[CH3:7]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 59292824HCID 59292824, compound

Product 1

HCID 59292845HCID 59292845, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-20 °C

Procedure

Sulfuryl chloride (75 μL, 0.93 mmol) was added dropwise to a cold (−20° C.) solution of 5-(2-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester (Step 176.3) (330 mg, 0.93 mmol) in CH3CN (6 mL). The reaction mixture was stirred for 10 min at −20° C., quenched by addition of a saturated solution of NaHCO3, and concentrated. The residue was diluted in EtOAc and a saturated solution of NaHCO3. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2) to provide 240 mg of the title compound as a white solid. Title compound: ESI-MS: 390.1 [M+H]+; tR=3.98 min (System 1); TLC: Rf=0.15 (Hex/EtOAc, 3:2).

Workup

  1. customquenched by addition of a saturated solution of NaHCO3
  2. concentrationconcentrated
  3. additionThe residue was diluted in EtOAc
  4. customThe aqueous phase was separated
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with H2O and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

Sources & evidence

ORD record
ord-a322d60504e44acb89242751aee41c19
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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