Pyrrole → HCID 22053427, compound

HRID 2416600Notes

Reaction equation

HRID 2416600 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[H-].[Na+].[OH-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)[CH:7]=1

Participants

6

Reactant 4

HCID 8027PyrroleHCID 14798Sodium HydroxideHCID 169882,3-DichloropyridineHCID 24758Sodium hydride

Product 1

HCID 22053427HCID 22053427, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.5 dichloropyridine (10.0 g, 67.6 mmol), pyrrole (5.50 g, 81.1 mmol), sodium hydride 60% (3.52 g, 87.9 mmol) and dimethyl sulfoxide (50 ml) was stirred at 70° C. for 2 h. Aqueous sodium hydroxide (200 ml, 1 M) was added and the mixture was extracted three times with diethyl ether (100 ml). The mixture was evaporated and, purified by chromatography on silica gel with dichloromethane and ethanol (4%) as solvent. Yield 6.3 g, 52%. Mp 70.5-72.0° C.

Workup

  1. extractionthe mixture was extracted three times with diethyl ether (100 ml)
  2. customThe mixture was evaporated
  3. custompurified by chromatography on silica gel with dichloromethane and ethanol (4%) as solvent

Sources & evidence

ORD record
ord-8a185727edec47ab86578a98728774fd
Source dataset
uspto-grants-2004_11
Patent number
US06825189B1

Reaction notes

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