Hydrochloric Acid → HCID 57709574, compound

HRID 2075808Notes

Reaction equation

HRID 2075808 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=O)[CH:5]=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:7]2.ClS([N:23]=C=O)(=O)=O.Cl>C(#N)C.CO>[NH2:23][C:4]1[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[N:7]=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 70918Chlorosulfonyl isocyanateHCID 826769Ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate

Product 1

HCID 57709574HCID 57709574, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A 12-L three-neck flask equipped with a mechanical mixer, a condenser, and thermocouple was charged with Compound 4 (0.94 mole, 269.1 g) in acetonitrile (ACN; about 4 L), after which chlorosulfonyl isocyanate (0.99 mole, 86 mL) was added (dropwise) via the dropping funnel. Upon completion of the addition, the resulting reaction mixture was refluxed for about 28 minutes. The pH of the mixture was about 0 at this point. The mixture then was cooled slightly, while adding saturated HCl in methanol (MeOH; 500 mL). Subsequently, the mixture was refluxed for about 1 hour, and then allowed to cool to room temperature overnight, during which time crystals formed. The crystals were collected on a sintered glass frit and rinsed with acetonitrile (400 mL and 500 mL). The filter cake was then transferred to a 12 L reactor with a mechanical stirrer. Deionized (DI) water (900 mL) and saturated Na2CO3 (500 mL) were added to afford mixture having a pH of about 10. Next, the solids in the mixture were collected and slurry rinsed with DI water (3×500 mL). The rinsed product was dried via lyophilization to afford about 268.79 g (63.3% yield) of Compound 5.

Workup

  1. customA 12-L three-neck flask equipped with a mechanical mixer, a condenser
  2. additionUpon completion of the addition
  3. customthe resulting reaction mixture
  4. temperaturewas refluxed for about 28 minutes
  5. temperatureThe mixture then was cooled slightly
  6. temperatureSubsequently, the mixture was refluxed for about 1 hour
  7. customformed
  8. customThe crystals were collected on a sintered glass frit
  9. washrinsed with acetonitrile (400 mL and 500 mL)
  10. customThe filter cake was then transferred to a 12 L reactor with a mechanical stirrer
  11. additionDeionized (DI) water (900 mL) and saturated Na2CO3 (500 mL) were added
  12. customto afford mixture
  13. customNext, the solids in the mixture were collected
  14. washslurry rinsed with DI water (3×500 mL)
  15. customThe rinsed product was dried via lyophilization

Sources & evidence

ORD record
ord-35a6c801e5a146adb62fe5c49a6815bc
Source dataset
uspto-grants-2011_04
Patent number
US07923458B2

Reaction notes

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