Acetone → HCID 15572316, compound

HRID 2286584Notes

Reaction equation

HRID 2286584 reaction equation
C(S[C:5]1[NH:6][C:7]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:9]=1[CH2:10][CH:11]=[CH2:12])(=O)C.CC(C)=O>[Ni].C(O)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:8]2[C:9]([CH2:10][CH2:11][CH3:12])=[CH:5][NH:6][C:7]=2[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 180AcetoneHCID 15572315HCID 15572315, compound

Product 1

HCID 15572316HCID 15572316, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5 g Raney nickel, 0.8 g (2 m moles) of 2-acetylthio-3-allyl-4,5-bis(4-chlorophenyl)pyrrole and 50 ml acetone was heated at reflux under nitrogen for two hours. The mixture was diluted with ethanol and the catalyst was removed by filtration. The filtrate was concentrated by rotary evaporation. The residue was purified by chromatography on 50 g Silic AR CC-7, eluting with hexane/toluene (90/10), to give 0.15 g of white crystals, m.p. 90°-93°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for two hours
  3. customthe catalyst was removed by filtration
  4. concentrationThe filtrate was concentrated by rotary evaporation
  5. customThe residue was purified by chromatography on 50 g Silic AR CC-7
  6. washeluting with hexane/toluene (90/10)

Sources & evidence

ORD record
ord-3327eb3582ad4b8fac6b2dee5c1fb4e8
Source dataset
uspto-grants-1981_05
Patent number
US04267184

Reaction notes

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