Thionyl Chloride → HCID 22024978, compound

HRID 1792820Notes

Reaction equation

HRID 1792820 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:12]([CH3:13])=[CH:11][N:10]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[N:19]3)[CH:9]=1)(O)=[O:6]>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][C:5]([C:8]1[C:12]([CH3:13])=[CH:11][N:10]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[N:19]3)[CH:9]=1)=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22024991HCID 22024991, compound

Product 1

HCID 22024978HCID 22024978, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

8 mL (110 mmol) of sulphinyl chloride are added to 0.47 g (1.86 mmol) of 3-carboxy-4-methyl-1-(quinolin-5-yl)-1H-pyrrole dissolved in 25 mL of chloroform at a temperature in the region of 20° C. under an argon atmosphere. After stirring for 1.5 hours at the reflux temperature of the solvent, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in 25 mL of chloroform and then concentrated to dryness again, giving 0.58 g (1.86 mmol) of 3-chlorocarbonyl-4-methyl-1-(quinolin-5-yl)-1H-pyrrole hydrochloride in the form of a beige-colored solid, which is used directly in the following step.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. dissolutionThe residue is dissolved in 25 mL of chloroform
  3. concentrationconcentrated to dryness again

Sources & evidence

ORD record
ord-b00e031520ad46b79cebee264b8977d5
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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