Iodoethane → 2-Ethylthio-4,5-bis-phenylthiazole

HRID 544641Notes

Reaction equation

HRID 544641 reaction equation
[C:1]1([C:7]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[S:10][C:9](=[S:18])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:21][CH2:22]CCCC.C(I)C>CN(C)P(=O)(N(C)C)N(C)C>[CH2:21]([S:18][C:9]1[S:10][C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)[CH3:22]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8058HexaneHCID 24758Sodium hydrideHCID 132096534,5-Bis-phenylthiazoline-2-thione

Product 1

HCID 132096572-Ethylthio-4,5-bis-phenylthiazole

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

5 g of 4,5-bis-phenylthiazoline-2-thione are dissolved in 50 ml of hexamethylphosphoric acid triamide, the solution is cooled to 5° and, while stirring, sodium hydride (0.89 g of a 50% strength suspension in mineral oil, de-oiled with hexane) is added. The mixture is stirred for 30 minutes at room temperature, then 3.18 g of ethyl iodide are slowly added dropwise and the mixture is then stirred for 30 minutes at room temperature, poured onto 1000 ml of ice-water and extracted by shaking twice with diethyl ether. The ether phases are combined, washed with water, dried over magnesium sulphate and concentrated to dryness by evaporation. The remaining pale yellow oil is dissolved in 200 ml of toluene/hexane (1:1) and filtered through 10 g of silica gel. Concentration of the eluate by evaporation yields 2-ethylthio-4,5-bis-phenylthiazole in the form of an oil.

Workup

  1. temperaturethe solution is cooled to 5°
  2. stirringThe mixture is stirred for 30 minutes at room temperature
  3. stirringthe mixture is then stirred for 30 minutes at room temperature
  4. extractionextracted
  5. stirringby shaking twice with diethyl ether
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated to dryness by evaporation
  9. dissolutionThe remaining pale yellow oil is dissolved in 200 ml of toluene/hexane (1:1)
  10. filtrationfiltered through 10 g of silica gel
  11. customConcentration of the eluate by evaporation

Sources & evidence

ORD record
ord-f3e26a2c18624af09705317b458c68d6
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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