Pyridine → 5-(N-phenyloxycarbonyl-1,4-dihydro-4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole

HRID 1085245Notes

Reaction equation

HRID 1085245 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[CH2:13][CH2:12][S:11]3)=[CH:4][CH:3]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24].C(OCC)(=O)C.CCCCCC.CO>C(Cl)Cl.O>[C:26]1([O:25][C:23]([N:16]2[CH:21]=[CH:20][CH:19]([C:15]3[N:14]4[C:10]([S:11][CH2:12][CH2:13]4)=[N:9][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:18]=[CH:17]2)=[O:24])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 136398976-(4-Fluorophenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazoleHCID 21879739Ethyl acetate hexane methanol

Product 1

HCID 144059625-(N-phenyloxycarbonyl-1,4-dihydro-4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b]thiazoleYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

6-(4-Fluorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole(10.0 g, 0.0456 mol) and 11 ml (0.136 mol) of pyridine were dissolved in 150 ml of methylene chloride. To this cooled solution (10°) was added 20.35 g (0.13 mol) of phenyl chloroformate in 20 ml of methylene chloride under a nitrogen atmosphere. During the addition, the reaction pot temperature was not allowed to rise past 15°. After the addition, the reddish-colored solution was stirred at ambient temperature for 1.5 hours, then heated under reflux for an additional 15 minutes. Thin-layer chromatography (ethyl acetate/hexane/methanol, 15:1:0.1) showed the reaction to be complete. The reaction mixture was diluted with 200 ml of water and extracted with methylene chloride (3×100 ml). The organic layer was dried, then concentrated to yield 17.0 g (89%) of 5-(N-phenyloxycarbonyl-1,4-dihydro-4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole; m.p. 164°-166° (from acetone/hexane).

Workup

  1. additionDuring the addition
  2. customto rise past 15°
  3. additionAfter the addition
  4. temperatureheated
  5. temperatureunder reflux for an additional 15 minutes
  6. customthe reaction
  7. extractionextracted with methylene chloride (3×100 ml)
  8. customThe organic layer was dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-897900a2d90445f1b29c6951d173fba4
Source dataset
uspto-grants-1991_04
Patent number
US05008390

Reaction notes

Loading…