Water → HCID 20385516, compound

HRID 46765Notes

Reaction equation

HRID 46765 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][C:9](=[S:18])[NH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[H-].[K+].Br[CH:22](Br)[CH3:23].O>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]2[C:9]([S:18][CH2:22][CH2:23]2)=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 112011,1-DibromoethaneHCID 82127Potassium hydrideHCID 150461594,5-Di(2-pyridyl)-2-imidazolethiol

Product 1

HCID 20385516HCID 20385516, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 16.57 g (0.065 m) of 4,5-di(2-pyridyl)-1H-imidazole-2-thione in 150 ml of dimethylformamide was stirred at -15° (ice-methanol-dry ice) under nitrogen and 27 ml (6.2 g, 0.15 m) of a 24% suspension of potassium hydride in mineral oil was added gradually. After about 2 hours, a solution of 11.8 g (5.42 ml, 0.0634 m) of dibromoethane in 60 ml of dimethylformamide was added dropwise. The reaction mixture was allowed to attain room temperature overnight. The mixture was poured into 600 ml of water. The aqueous mixture was extracted with 3×200 ml portions of methylenechloride. The combined extracts were washed with 5×100 ml water, brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated under 25 ml of low boiling petroleum ether. The product was separated, dissolved in 50 ml of ethanol. The solution was chilled until crystallization was complete, filtered, and the product was washed with a small portion of cold ethanol and air dried. Yield 9.1 g, m.p. 140°-142°. Crystallization three times from ethanol gave an analytical sample of 5,6-di-(2-pyridyl)-2,3-dihydroimidazo[2,1-b]thiazole, m.p. 142°-143°.

Workup

  1. waitto attain room temperature overnight
  2. extractionThe aqueous mixture was extracted with 3×200 ml portions of methylenechloride
  3. washThe combined extracts were washed with 5×100 ml water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated under 25 ml
  7. customThe product was separated
  8. dissolutiondissolved in 50 ml of ethanol
  9. temperatureThe solution was chilled until crystallization
  10. filtrationfiltered
  11. washthe product was washed with a small portion of cold ethanol and air
  12. customdried
  13. customCrystallization three times from ethanol

Sources & evidence

ORD record
ord-8c0ce9aca69e4eb3944c74a2862b95ab
Source dataset
uspto-grants-1979_11
Patent number
US04175127

Reaction notes

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