Pyridine → HCID 14999088, compound

HRID 981557Notes

Reaction equation

HRID 981557 reaction equation
OCC[N:4]1[C:8](=[O:9])[CH:7]([CH3:10])[S:6][CH:5]1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>C(Cl)Cl>[CH3:10][CH:7]1[S:6][CH:5]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[NH:4][C:8]1=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 14999089HCID 14999089, compound

Product 1

HCID 14999088HCID 14999088, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-Hydroxyethyl)-5-methyl-2-(3-pyridyl)- thiazolidin-4-one (18.75 g, 78.7 mmol) was dissolved in methylene chloride (200 ml). Pyridine (9.55 ml, 118 mmol) was added and further, thionyl chloride (20 ml, 274 mmol) was added dropwise over 2 hours at 0 to 5° C. This reaction mixture was kept between those temperatures for 5 hours. The resulting mixture was washed with aqueous NaHCO3 and aqueous NaCl, dried, and the solvent was removed in vacuo. The residue was chromatographed on silica gel and upon recrystallization from hexane-ether, gave 2,5-cis-3-(2-chloroethyl)-5-methyl-2-(3-pyridyl)thiazolidin-4-one (7.11 g) and 2,5-2-chloroethyl)-5-methyl-2-(3-pyridyl)thiazolidin-4one (3.11 g), (51% yield).

Workup

  1. washThe resulting mixture was washed with aqueous NaHCO3 and aqueous NaCl
  2. customdried
  3. customthe solvent was removed in vacuo
  4. customThe residue was chromatographed on silica gel and upon recrystallization from hexane-ether

Sources & evidence

ORD record
ord-6db369387d37419dad6b5dee6eb5cebc
Source dataset
uspto-grants-1991_02
Patent number
US04992455

Reaction notes

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