Thiazolidine → HCID 17779975, compound

HRID 1392911Notes

Reaction equation

HRID 1392911 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[S:10]1[CH2:14][CH2:13][NH:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:12]2[CH2:13][CH2:14][S:10][CH2:11]2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10444ThiazolidineHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 17779975HCID 17779975, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (500 mg, 3.08 mmole) in 4 mL of dry acetonitrile is added 0.42 mL (6.17 mmol) of thiazolidine followed by 852 mg (6.17 mmol) of potassium carbonate. The reaction is heated at 80° C. for 20 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 275 mg (42% yield) of 2-Chloro-5-thiazolidin-3-ylmethyl-pyridine. Diagnostic C13 NMR (100 MHz, CDCl3) 29.8, 53.6, 57.7, 60.3, 112.4, 124.4, 133.3, 139.6, 150.1; MS 215.2 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is quenched with 5 mL of water
  3. extractionextracted three-times with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customConcentration of the solvent provided an oil which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-531726e50838497c9d62b8bf4dc89241
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

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