Pyridine → 1-[(4-Chlorophenyl)thio]-1-phenylacetone

HRID 1246392Notes

Reaction equation

HRID 1246392 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.Br[CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:17](=[O:19])[CH3:18]>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([CH3:18])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7815p-ChlorothiophenolHCID 908702-Propanone, 1-bromo-1-phenyl-

Product 1

HCID 219170461-[(4-Chlorophenyl)thio]-1-phenylacetone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 100 ml round-bottomed flask, 1 eq. of 4-chlorothiophenol is dissolved in 4 eq. of pyridine and 50 ml of anhydrous ether, with magnetic stirring. 1.2 eq. of bromophenylacetone are then added dropwise and stirring is then carried out overnight at ambient temperature. The reaction mixture is then poured onto ice-cold water and is extracted with ethyl acetate. The organic phase is washed with 1M HCl solution and then with water, is dried over MgSO4 and is evaporated under reduced pressure. The residue obtained is purified by chromatography on a silica gel column.

Workup

  1. additionThe reaction mixture is then poured onto ice-cold water
  2. extractionis extracted with ethyl acetate
  3. washThe organic phase is washed with 1M HCl solution
  4. dry with materialwith water, is dried over MgSO4
  5. customis evaporated under reduced pressure
  6. customThe residue obtained
  7. customis purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-516622ebbc8248aeb9d3d9014155c6ca
Source dataset
uspto-grants-2006_10
Patent number
US07126012B2

Reaction notes

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