Thionyl Chloride → 4,5-Dimethyl-1-(quinolin-4-yl)-1H-pyrrole-3-carbonyl chloride

HRID 1792811Notes

Reaction equation

HRID 1792811 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH:9]=1)(O)=[O:6]>C(Cl)(Cl)Cl>[Cl:3][C:5]([C:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH:9]=1)=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 220249714,5-Dimethyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 220249704,5-Dimethyl-1-(quinolin-4-yl)-1H-pyrrole-3-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10 mL (137 mmol) of sulphinyl chloride are added at a temperature in the region of 20° C. under an argon atmosphere to 1.1 g (4.1 mmol) of 3-carboxy-4,5-dimethyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 20 mL of chloroform. After stirring at the reflux point of the solvent for 1.5 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in 20 mL of chloroform and is then brought back to dryness to give 1.17 g (4.1 mmol) of 3-chlorocarbonyl-4,5-dimethyl-1-(quinol-4-yl)-1H-pyrrole in the form of a brown-yellow 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 20 mL of chloroform

Sources & evidence

ORD record
ord-7e005a6ec3d348a894d4a05f8676e56e
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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