Ethanol → 6-(4-Fluorophenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole

HRID 1085243Notes

Reaction equation

HRID 1085243 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=O)[CH2:7]Cl)=[CH:4][CH:3]=1.[NH2:12][C:13]1[S:14][CH2:15][CH2:16][N:17]=1.C(O)C>O>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:12]=[C:13]3[N:17]([CH:7]=2)[CH2:16][CH2:15][S:14]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 156894,5-Dihydro-2-thiazolamineHCID 1202482-Chloro-4'-fluoroacetophenone

Product 1

HCID 136398976-(4-Fluorophenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazoleYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 51.6 g (0.3 mol) of 4-fluorophenacylchloride, 33.66 g (0.33 mol) of 2-aminothiazoline and 200 ml of ethanol was heated at reflux for 2 hours. The mixture was cooled to room temperature at which point 300 ml of water was added. After a reflux period of 2 hours, the mixture was concentrated to remove about 190 ml of aqueous alcohol. The pH of the residue was adjusted to about 2 with 10% hydrochloric acid (10 ml). The solid product was separated and dried to give 65.4 g (85%) of 6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole, m.p. 116-118°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. additionwas added
  4. concentrationthe mixture was concentrated
  5. customto remove about 190 ml of aqueous alcohol
  6. customThe solid product was separated
  7. customdried

Sources & evidence

ORD record
ord-f58c4174469045b382dca4fb2bbeb62a
Source dataset
uspto-grants-1991_04
Patent number
US05008390

Reaction notes

Loading…