HCID 69344187, compound → HCID 69344274, compound

HRID 1373422Notes

Reaction equation

HRID 1373422 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[S:8][CH:9]=[CH:10][C:11]=1[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.[Cu](C#N)[C:18]#[N:19]>CN(C)C=O.Cl.[Fe](Cl)Cl>[C:18]([C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[S:8][CH:9]=[CH:10][C:11]=1[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)#[N:19]

Participants

6

Reactant 2

HCID 69344187HCID 69344187, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 69344274HCID 69344274, compound

Reagents, catalysts & solvents 3

HCID 24458Ferrous ChlorideCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

10 mmol of 3-bromoterthiophene was refluxed in anhydrous dimethylformamide (10 ml) containing 15 mmol of copper cyanide for 4 hours. After the dark mixture was allowed to cool to room temperature it was mixed with iron chloride (10 g) in hydrochloric acid solution (20 ml, 2.0M) and maintained at 60˜70° C. for 30 minutes. The organic extract was washed with hydrochloric acid solution (20 ml, 6M), distilled water, saturated sodium bicarbonate solution and aqueous sodium chloride solution to obtain a dark yellowish solid. The obtained solid was recrystallized from an organic solvent. The product has a melting point of 83° C. and a molecular weight of 272.9736 g/mol as measured using a mass spectrometer. The structure of the product was identified through 13C NMR, 1H NMR, and IR spectrometer.

Workup

  1. temperaturemaintained at 60˜70° C. for 30 minutes
  2. extractionThe organic extract
  3. washwas washed with hydrochloric acid solution (20 ml, 6M)
  4. distillationdistilled water, saturated sodium bicarbonate solution and aqueous sodium chloride solution
  5. customto obtain a dark yellowish solid
  6. customThe obtained solid was recrystallized from an organic solvent

Sources & evidence

ORD record
ord-9f32c1112a6a48c9a3ee01c255849c2a
Source dataset
uspto-grants-2007_01
Patent number
US07161013B2

Reaction notes

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