Water → HCID 66584592, compound

HRID 1629978Notes

Reaction equation

HRID 1629978 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:13]#[N:14])=[CH:10][NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:15]N1C(=O)CCC1=O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[Cl:15][C:12]1[NH:11][CH:10]=[C:9]([C:13]#[N:14])[C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 534262514-(3-Fluorophenyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 66584592HCID 66584592, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 41.0 g (220 mmol) of 4-(3-fluorophenyl)-1H-pyrrole-3-carbonitrile in 400 ml of tetrahydrofuran are added portionwise 33.0 g (242 mmol) of N-chlorosuccinimide (CAS 128-09-6) and the mixture is then stirred for 24 hours at reflux. After cooling, 200 ml of water containing 5 g of sodium thiosulfate are added and, after stirring for 5 minutes, 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 45.5 g of 5-chloro-4-(3-fluorophenyl)-1H-pyrrole-3-carbonitrile in the form of a whitish powder after triturating in 200 ml of dichloromethane, filtering off and drying.

Workup

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

Sources & evidence

ORD record
ord-f4be3078f42d463ea14f00164d455070
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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