Ethanol → 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5,6-diphenyl imidazo[2,1-b]thiazole

HRID 980352Notes

Reaction equation

HRID 980352 reaction equation
[Na].[C:2]1([C:8]2[N:9]=[C:10]([SH:19])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([C:24]1[CH:25]=[C:26]([CH:31]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:33]=1)[C:27](=O)[CH2:28]Br)([CH3:23])([CH3:22])[CH3:21].C([OH:40])C>>[C:20]([C:24]1[CH:25]=[C:26]([C:27]2[N:9]3[C:8]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[C:12]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:11]=[C:10]3[S:19][CH:28]=2)[CH:31]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:33]=1[OH:40])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 4

HCID 702EthanolHCID 5360545SodiumHCID 202223723,5-Di-tert-butylphenacyl bromideHCID 178527825HCID 178527825, compound

Product 1

HCID 137543273-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5,6-diphenyl imidazo[2,1-b]thiazole

Procedure

In 20 ml of ethanol was dissolved 0.11 g of metallic sodium and after adding 1 g of 4,5-diphenyl-2-mercaptoimidazole to the solution followed by stirring several minutes, 1 g of 3,5-di-tert-butylphenacyl bromide was added thereto followed by stirring for one hour at room temperature. The reaction mixture was concentrated udner reduced pressure and then water was added to the residue. The crystals thus formed were recovered by filtration, dried, dissolved in 20 ml of phosphorus oxychloride, and the solution was refluxed for 14 hours. The reaction mixture was concentrated under reduced pressure and after adding water to the residue followed by neutralization with potassium carbonate, the product was extracted with chloroform. The extract was dried and concentrated. The residue was subjected to silica gel column chromatography and the product was eluted with chloroform. The crude crystals thus obtained were recrystallized from ethanol to provide 0.8 g of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5,6-diphenyl imidazo[2,1-b]thiazole.

Workup

  1. stirringby stirring for one hour at room temperature
  2. concentrationThe reaction mixture was concentrated udner reduced pressure
  3. additionwater was added to the residue
  4. customThe crystals thus formed
  5. filtrationwere recovered by filtration
  6. customdried
  7. dissolutiondissolved in 20 ml of phosphorus oxychloride
  8. temperaturethe solution was refluxed for 14 hours
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. additionafter adding water to the residue
  11. extractionthe product was extracted with chloroform
  12. customThe extract was dried
  13. concentrationconcentrated
  14. washthe product was eluted with chloroform
  15. customThe crude crystals thus obtained
  16. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-33ff80760b854071becfc68346021a8c
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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