Sodium Iodide → HCID 13749533, compound

HRID 867902Notes

Reaction equation

HRID 867902 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])=[S:4].Cl.Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH:25]=[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:19][CH2:20][N:21]1[CH2:22][CH:23]=[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH2:25][CH2:26]1)=[S:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 137495312-(2-Hydroxyphenyl)-N-methyl-1,3-thiazolidine-3-carbothioamideHCID 21289053HCID 21289053, compound2×

Product 1

HCID 13749533HCID 13749533, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.27 g of N-methyl-2-(2-hydroxyphenyl)thiazolidine-3-carbothioamide, 1.38 g of 1-(2-chloroethyl)-4-(3-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride, 1.50 g of potassium carbonate, 0.75 g sodium iodide and 25 ml of dimethylformamide is stirred at 90° C. for 8 hours. 0.7 g of 1-(2-chloroethyl)-4-(3-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride is added to the reaction mixture, and the mixture is further stirred at the same temperature for 15 hours. The mixture is evaporated under reduced pressure to remove the solvent. Water is added to the residue, and the aqueous solution is extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent, chloroform:ethanol=45:1), whereby 0.39 g of N-methyl-2-{2-[2-(4-(3-fluorophenyl)-1,2,3,6-tetrahydropyridin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide is obtained.

Workup

  1. stirringthe mixture is further stirred at the same temperature for 15 hours
  2. customThe mixture is evaporated under reduced pressure
  3. customto remove the solvent
  4. additionWater is added to the residue
  5. extractionthe aqueous solution is extracted with ethyl acetate
  6. washThe extract is washed with water
  7. customdried
  8. customevaporated
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography (solvent, chloroform:ethanol=45:1)

Sources & evidence

ORD record
ord-bed9a278bc9d4e238875e31481b127f4
Source dataset
uspto-grants-1988_10
Patent number
US04777178

Reaction notes

Loading…