Water → HCID 66584709, compound

HRID 589849Notes

Reaction equation

HRID 589849 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-fc9a940150c24b4ea2b91a4c5c3b79d0
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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