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

HRID 1381682Notes

Reaction equation

HRID 1381682 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.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:23]1([C:22]([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:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chloride2×HCID 136398976-(4-Fluorophenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole

Product 1

HCID 144059635-(N-phenylcarbonyl-1,4-dihydro-4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo-[2,1-b]thiazoleYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-(4-Fluorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole (45.0 g, 0.204 mol) and 55 ml (0.68 mol) of pyridine were dissolved in 500 ml of methylene chloride. To this cooled (ice water bath) solution (10°) was added 91.3 g (0.65 mol) of benzoyl chloride in 100 ml of methylene chloride under a nitrogen atmosphere. During the addition, the reaction pot temperature was not allowed to rise past 10°. After the addition, the desired product precipitated from solution. The addition of the benzoyl chloride solution was continued. The resulting suspension was stirred at ambient temperature for 15 minutes, then heated to reflux for 15 minutes. Thin-layer chromatography (ethyl acetate/hexane/methanol, 15:1:0.1) showed the presence of some starting material. An additional 20 ml of pyridine followed by benzoyl chloride (28 g, 0.2 mol) were added at room temperature. The suspension was stirred for an additional 0.5 hour. Analysis did not detect starting material at this time. The reaction suspension was filtered. The collected solid was washed with petroleum ether. The solid was vacuum dried to yield 66.8 g (81%) of 5-(N-phenylcarbonyl-1,4-dihydro-4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo-[2,1-b]thiazole; m.p. 188°-189°.

Workup

  1. additionDuring the addition
  2. customto rise past 10°
  3. additionAfter the addition
  4. customthe desired product precipitated from solution
  5. additionThe addition of the benzoyl chloride solution
  6. temperatureheated
  7. temperatureto reflux for 15 minutes
  8. additionwere added at room temperature
  9. stirringThe suspension was stirred for an additional 0.5 hour
  10. filtrationThe reaction suspension was filtered
  11. washThe collected solid was washed with petroleum ether
  12. customdried

Sources & evidence

ORD record
ord-18fcd3830143408792c6ee2787a1e7bf
Source dataset
uspto-grants-1989_02
Patent number
US04803279

Reaction notes

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