Acetonitrile → 5,6-Bis(p-anisyl)-2,3-dihydroimidazo[2,1-b]thiazole

HRID 444286Notes

Reaction equation

HRID 444286 reaction equation
Br[CH:2]([C:13]1[CH:20]=[CH:19][C:16](OC)=[CH:15][CH:14]=1)[C:3](=O)[C:4]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[CH:6][CH:5]=1.[NH2:21][C:22]1[S:23][CH2:24][CH2:25][N:26]=1.[C:27](=[O:30])([O-])[O-].[K+].[K+].[C:33](#N)[CH3:34]>>[CH2:20]([C:13]1[N:26]2[C:22]([S:23][CH2:24][CH2:25]2)=[N:21][C:2]=1[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[CH:10][CH:11]=1)[C:19]1[CH:16]=[CH:15][C:14]([O:30][CH3:27])=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 156894,5-Dihydro-2-thiazolamineHCID 3441532-Bromo-1,2-bis(4-methoxyphenyl)ethanone

Product 1

HCID 571019865,6-Bis(p-anisyl)-2,3-dihydroimidazo[2,1-b]thiazole

Procedure

A suspension of 145 g. (0.433 mole) of α-bromodesoxy-p-anisoin, 88.36 g. (0.865 mole) of finely powdered 2-amino-4,5-dihydrothiazole and 179.5 g. (1.3 moles) of pulverized potassium carbonate in 1.0 liter of sieve dried acetonitrile under nitrogen was stirred at 25° C. for 3 days. The solvent was evaporated in vacuo and the residue treated with methylene chloride and 5% aqueous sodium carbonate. The organic phase was removed, washed once with 10% aqueous sodium carbonate, 3 times with water, dried over potassium carbonate, filtered and evaporated in vacuo. A solution of the residue dissolved in methylene chloride was treated with charcoal, filtered and hexane added. The precipitate was filtered and recrystallized from methylene chloride to give 5,6-bis(p-anisyl)-2,3-dihydroimidazo[2,1-b]thiazole.

Workup

  1. additionA suspension of 145 g
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue treated with methylene chloride and 5% aqueous sodium carbonate
  4. customThe organic phase was removed
  5. washwashed once with 10% aqueous sodium carbonate, 3 times with water
  6. dry with materialdried over potassium carbonate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. dissolutionA solution of the residue dissolved in methylene chloride
  10. additionwas treated with charcoal
  11. filtrationfiltered
  12. additionhexane added
  13. filtrationThe precipitate was filtered
  14. customrecrystallized from methylene chloride

Sources & evidence

ORD record
ord-113353e41b104b6a84543cab5c30d28e
Source dataset
uspto-grants-1981_04
Patent number
US04263311

Reaction notes

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