Potassium Iodide → 4'-{[2-[4-(p-fluorophenyl)-3,6-dihydro-1(2H)-pyridyl]-ethyl]thio}acetanilide

HRID 1605955Notes

Reaction equation

HRID 1605955 reaction equation
Cl[CH2:2][CH2:3][S:4][C:5]1[CH:14]=[CH:13][C:8]([NH:9][C:10](=[O:12])[CH3:11])=[CH:7][CH:6]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C(O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][S:4][C:5]3[CH:14]=[CH:13][C:8]([NH:9][C:10](=[O:12])[CH3:11])=[CH:7][CH:6]=3)[CH2:24][CH:23]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1977484-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridineHCID 197003694'-[(2-Chloroethyl)thio]acetanilide

Product 1

HCID 215456214'-{[2-[4-(p-fluorophenyl)-3,6-dihydro-1(2H)-pyridyl]-ethyl]thio}acetanilide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.8 G. of 4'-[(2-chloroethyl)thio]acetanilide, 2.7 g. of 4-(p-fluorophenyl)-1,2,3,6-tetrahydropyridine, 4.5 g. of potassium carbonate and a few crystals of potassium iodide are heated under reflux conditions in 50 ml. of ethanol and 5 ml. of water for 16 hours. The solvent is evaporated under reduced pressure, the residue is taken up in chloroform and washed with water. From the organic phase there is obtained crude 4'-{[2-[4-(p-fluorophenyl)-3,6-dihydro-1(2H)-pyridyl]-ethyl]thio}acetanilide which melts at 150°-152°C. after recrystallization from acetic acid ethyl ester.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. washwashed with water

Sources & evidence

ORD record
ord-feec41f8f5934a3d9e43a861cc7ed94f
Source dataset
uspto-grants-1976_04
Patent number
US03951987

Reaction notes

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