Pyridine → HCID 13209657, compound

HRID 544642

Reaction equation

HRID 544642 reaction equation
N1C=CC=[CH:3][CH:2]=1.Br[CH:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.C([NH:25][C:26](=[S:28])[S-:27])C>C(O)C>[CH2:2]([S:27][C:26]1[S:28][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:25]=1)[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1026302-Bromo-1,2-diphenylethan-1-oneHCID 18544323HCID 18544323, compound

Product 1

HCID 13209657HCID 13209657, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.106 g of pyridine and 3.68 g of 2-bromo-1,2-bis-phenylethanone are added while stirring to a solution, cooled to 5°, of 1.694 g of ethyldithiocarbamate in 25 ml of ethanol. The mixture is then stirred for 30 minutes at 5° and for 90 minutes at room temperature, concentrated to dryness by evaporation under reduced pressure, and the residue is partitioned between methylene chloride and water. The aqueous phase is acidified with N hydrochloric acid and extracted by shaking again twice with methylene chloride. The organic phases are combined, dried over magnesium sulphate and concentrated to dryness by evaporation under reduced pressure. The remaining oil is purified by chromatography over 100 g of silica gel with toluene/hexane (1:1) as eluant. Concentration by evaporation yields 2-ethylthio-4,5-bis-phenylthiazole in the form of an oil.

Workup

  1. stirringThe mixture is then stirred for 30 minutes at 5° and for 90 minutes at room temperature
  2. concentrationconcentrated to dryness by evaporation under reduced pressure
  3. customthe residue is partitioned between methylene chloride and water
  4. extractionextracted
  5. stirringby shaking again twice with methylene chloride
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated to dryness by evaporation under reduced pressure
  8. customThe remaining oil is purified by chromatography over 100 g of silica gel with toluene/hexane (1:1) as eluant
  9. concentrationConcentration
  10. customby evaporation

Sources & evidence

ORD record
ord-71fb122494914043824b8ddf4b515978
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Linked notes

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