Water → HCID 66584709, compound

HRID 1629994Notes

Reaction equation

HRID 1629994 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[Cl:18]N1C(=O)CCC1=O.O>O1CCCC1>[Cl:18][C:13]1[NH:12][CH:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 66584156HCID 66584156, compound

Product 1

HCID 66584709HCID 66584709, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 16.5 g (72.9 mmol) of methyl 4-(3-cyano-phenyl)-1H-pyrrole-3-carboxylate in 150 ml of tetrahydrofuran are added portionwise 9.93 g (74.4 mmol) of N-chlorosuccinimide (CAS 128-09-6) and the mixture is then stirred for 6 hours at reflux. After cooling, 250 ml of water are added and the reaction product is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give 17.1 g of methyl 5-chloro-4-(3-cyanophenyl)-1H-pyrrole-3-carboxylate in the form of a beige-coloured powder after recrystallizing from acetonitrile, filtering off and drying.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. extractionthe reaction product is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-5ed6c27cf8804bae81668e4a66b3f20c
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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