2-Bromo-1,2-bis(4-methoxyphenyl)ethanone → 1,2-Bis-(p-methoxyphenyl)-2-isothiocyanoethanone

HRID 544650Notes

Reaction equation

HRID 544650 reaction equation
Br[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].[S-:21][C:22]#[N:23].[Na+]>C(O)C>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH:2]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:23]=[C:22]=[S:21])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3441532-Bromo-1,2-bis(4-methoxyphenyl)ethanoneHCID 516871Sodium thiocyanate

Product 1

HCID 204583321,2-Bis-(p-methoxyphenyl)-2-isothiocyanoethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 g of 2-bromo-1,2-bis-(p-methoxyphenyl)-ethanone are mixed with 700 ml of 96% strength ethanol and 25.4 g of sodium thiocyanate and the mixture is heated at 45° for 2 hours. The mixture is then concentrated to dryness by evaporation under reduced pressure, 500 ml of ice-water are added, the mixture is filtered with suction and the residue is then washed twice with ice-water. The crude product is taken up in 1500 ml of methylene chloride, the remaining water is removed and the product is dried over magnesium sulphate. The product is then concentrated to approximately 200 ml, allowed to cool, filtered with suction again, then washed with a little methylene chloride and dried under reduced pressure. 1,2-bis-(p-methoxyphenyl)-2-isothiocyano-ethanone having a melting point of 155° is obtained.

Workup

  1. temperaturethe mixture is heated at 45° for 2 hours
  2. concentrationThe mixture is then concentrated to dryness by evaporation under reduced pressure, 500 ml of ice-water
  3. additionare added
  4. filtrationthe mixture is filtered with suction
  5. washthe residue is then washed twice with ice-water
  6. customthe remaining water is removed
  7. dry with materialthe product is dried over magnesium sulphate
  8. concentrationThe product is then concentrated to approximately 200 ml
  9. temperatureto cool
  10. filtrationfiltered with suction again
  11. washwashed with a little methylene chloride
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd49bb793d484c6a87a2b4bdb4664bf1
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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