2-Naphthalenethiol → 3-(Naphth-2-ylthio)propiophenone

HRID 1614247Notes

Reaction equation

HRID 1614247 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[SH:11].Br[CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].[OH-].[Na+]>CN(C)C=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]

Participants

5

Reactant 3

HCID 70582-NaphthalenethiolHCID 14798Sodium HydroxideHCID 1224323-Bromo-1-phenylpropan-1-one

Product 1

HCID 126670543-(Naphth-2-ylthio)propiophenoneYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-naphthalenethiol (12.94 g), 3-bromopropiophenone (17.35 g), cuprous oxide (5.83 g), sodium hydroxide (3.24 g) and dimethylformamide (130 ml) was heated to reflux for 18 hours. The mixture was concentrated and the residue was partitioned between diethyl ether and water. The organic phase was dried (MgSO4) and evaporated. The residue was dissolved in a mixture of ethyl acetate and hexane and treated with charcoal. The solution was filtered and evaporated. The residue was recrystallised from a mixture of methanol and water to give 3-(naphth-2-ylthio)propiophenone (5.23 g, 22%), m.p. 90°-91° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. concentrationThe mixture was concentrated
  4. customthe residue was partitioned between diethyl ether and water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated
  7. dissolutionThe residue was dissolved in a mixture of ethyl acetate and hexane
  8. additiontreated with charcoal
  9. filtrationThe solution was filtered
  10. customevaporated
  11. customThe residue was recrystallised from a mixture of methanol and water

Sources & evidence

ORD record
ord-5990f9867e2f427e9627a3e70e6c7e4a
Source dataset
uspto-grants-1993_03
Patent number
US05196422

Reaction notes

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