Water → 5-Phenyl-4-(3-pyridyl)-thiazoline-2-thione

HRID 544646Notes

Reaction equation

HRID 544646 reaction equation
Br.Br[CH:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=O.[C:18](=[S:21])([S-:20])[NH2:19].[NH4+].O.[OH-].[Na+]>CO>[C:12]1([CH:3]2[S:21][C:18](=[S:20])[N:19]=[C:4]2[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 11083854Ammonium dithiocarbamateHCID 134660052-Bromo-2-phenyl-1-(3-pyridyl)ethanone hydrobromide

Product 1

HCID 132096555-Phenyl-4-(3-pyridyl)-thiazoline-2-thione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

42.0 g of the 2-bromo-2-phenyl-1-(3-pyridyl)-ethanone hydrobromide so obtained are dissolved, while stirring, in 500 ml of methanol (95% strength), the solution is cooled to 10° and, in the course of 5 minutes, 14.93 g of ammonium dithiocarbamate are added in portions. The mixture is cooled for a further 5 minutes, the ice-bath is removed, after 45 minutes again 14.93 g of ammonium dithiocarbamate are added and the mixture is then heated at the boil for 90 minutes and concentrated to dryness by evaporation. The residue obtained by concentration by evaporation is digested with 200 ml of water and 65 ml of 2 N sodium hydroxide solution, filtered with suction and washed with a little water. The product is dissolved in 100 ml of 2 N sodium hydroxide solution, filtered and acidified to pH 5 with 2 N hydrochloric acid. The precipitated crystals are filtered with suction, washed twice with a little ice-water, sucked dry, and then thoroughly washed twice with 30 ml of acetone each time and then twice with 50 ml of diethyl ether each time. 5-Phenyl-4-(3-pyridyl)-thiazoline-2-thione having a melting point of 229°-232° is obtained.

Workup

  1. dissolutionare dissolved
  2. additionare added in portions
  3. temperatureThe mixture is cooled for a further 5 minutes
  4. customthe ice-bath is removed, after 45 minutes again 14.93 g of ammonium dithiocarbamate
  5. additionare added
  6. temperaturethe mixture is then heated at the boil for 90 minutes
  7. concentrationconcentrated to dryness by evaporation
  8. customThe residue obtained by concentration by evaporation
  9. filtrationfiltered with suction
  10. washwashed with a little water
  11. dissolutionThe product is dissolved in 100 ml of 2 N sodium hydroxide solution
  12. filtrationfiltered
  13. filtrationThe precipitated crystals are filtered with suction
  14. washwashed twice with a little ice-water
  15. customsucked dry
  16. washthoroughly washed twice with 30 ml of acetone each time

Sources & evidence

ORD record
ord-131bb91aff954a788146f508e7cb216b
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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