2-Bromo-1,2-bis(4-methoxyphenyl)ethanone → 4,5-Bis-(p-methoxyphenyl)-thiazoline-2-thione

HRID 544648Notes

Reaction equation

HRID 544648 reaction equation
C(=S)([O-])N.[NH4+].Br[CH:7]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=O.[C:26](=[S:29])([S-:28])[NH2:27].[NH4+]>C(O)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[CH:7]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[S:29][C:26](=[S:28])[N:27]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 3441532-Bromo-1,2-bis(4-methoxyphenyl)ethanoneHCID 11083854Ammonium dithiocarbamateHCID 178514131azanium sulfanylmethanimidate

Product 1

HCID 132096564,5-Bis-(p-methoxyphenyl)-thiazoline-2-thione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.92 g of ammonium thiocarbamate are suspended in 70 ml of 96% strength ethanol. The suspension is cooled to 5° and, while stirring, 15 g of 2-bromo-1,2-bis-(p-methoxyphenyl)-ethanone are added thereto in portions in the course of 10 minutes, the internal temperature being maintained at approximately 10° by cooling. The mixture is then stirred for 1 hour at 10°, a further 2.4 g of ammonium dithiocarbamate are added and stirring is carried out again for 3 hours at room temperature. The mixture is then poured into 500 ml of ice-water, the crude product is filtered off with suction and then washed with ice-water. For purification, the crude product is suspended in 50 ml of ethanol and heated under reflux, first of all dissolution occurring and, after 90 minutes, reprecipitation. The whole is allowed to cool, filtered with suction and the residue is then washed with cold ethanol. 4,5-bis-(p-methoxyphenyl)-thiazoline-2-thione having a melting point of 226°-230° is obtained.

Workup

  1. temperatureThe suspension is cooled to 5°
  2. temperaturein portions in the course of 10 minutes, the internal temperature being maintained at approximately 10°
  3. temperatureby cooling
  4. stirringThe mixture is then stirred for 1 hour at 10°
  5. stirringstirring
  6. filtrationthe crude product is filtered off with suction
  7. washwashed with ice-water
  8. customFor purification
  9. temperatureheated
  10. temperatureunder reflux, first of all dissolution
  11. waitoccurring and, after 90 minutes
  12. customreprecipitation
  13. temperatureto cool
  14. filtrationfiltered with suction
  15. washthe residue is then washed with cold ethanol

Sources & evidence

ORD record
ord-b2dacf5ccc8748158d565bfd8d833dd4
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

Loading…