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

HRID 444285Notes

Reaction equation

HRID 444285 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][CH2:5][N:6]=1.[CH3:7][OH:8].Br[CH:10]([C:21]1[CH:28]=[CH:27][C:24](OC)=[CH:23][CH:22]=1)[C:11](=O)[C:12]1[CH:19]=[CH:18][C:15]([O:16][CH3:17])=[CH:14][CH:13]=1.[C:29](#N)[CH3:30]>>[CH2:28]([C:21]1[N:6]2[C:2]([S:3][CH2:4][CH2:5]2)=[N:1][C:10]=1[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[CH:18][CH:19]=1)[C:27]1[CH:24]=[CH:23][C:22]([O:8][CH3:7])=[CH:30][CH:29]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6342AcetonitrileHCID 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

2-Amino-4,5-dihydrothiazole (10.2 g.) in 50 ml. of methanol was added to a stirred solution of 33.5 g. of α-bromodesoxy-p-anisoin in 200 ml. of acetonitrile in a nitrogen atmosphere. After 2-3 days at room temperature, the solution was evaporated in vacuo. The residue was partitioned between 200 ml. of methylene chloride and 10% aqueous sodium carbonate solution. The organic solution was washed twice with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was recrystallized twice from acetonitrile to give 5,6-bis(p-anisyl)-2,3-dihydroimidazo[2,1-b]thiazole, m.p. 154.5°-156.5° C.

Workup

  1. customthe solution was evaporated in vacuo
  2. customThe residue was partitioned between 200 ml
  3. washThe organic solution was washed twice with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was recrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-5e92b5dc3f9a4655a569294f7b5cc033
Source dataset
uspto-grants-1981_04
Patent number
US04263311

Reaction notes

Loading…