Thionyl Chloride → HCID 86627536, compound

HRID 1969933Notes

Reaction equation

HRID 1969933 reaction equation
S(Cl)(Cl)=O.[O:5]=[C:6]1[C:15]2[NH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:14]=2[C:13]2[CH:12]=[C:11]([S:22](=[O:31])(=[O:30])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:10]=[CH:9][C:8]=2[NH:7]1>C(O)C>[O:5]=[C:6]1[C:15]2[NH:16][CH:17]=[CH:18][C:14]=2[C:13]2[CH:12]=[C:11]([S:22](=[O:31])(=[O:30])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:10]=[CH:9][C:8]=2[NH:7]1.[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 451210694-oxo-8-phenylsulfamoyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627536HCID 86627536, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 20 μL (0.28 mmol) of thionyl chloride diluted in 0.5 mL of anhydrous ethanol is added dropwise to 27 mg (0.07 mmol) of 4-oxo-8-phenylsulfamoyl-4,5-dihydro-3H -pyrrolo[2,3-c]quinoline-1-carboxylic acid suspended in 0.5 mL of anhydrous ethanol. The solution is stirred under reflux for 72 hours then cooled to room temperature. The solid is filtered to give 3.5 mg (12%) of 4-oxo-8-phenylsulfamoyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. temperatureunder reflux for 72 hours
  2. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-e882c988ae884491a91cd2e9e934a787
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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