Potassium Carbonate → 3-(2-Chloro-5-pyridylmethyl)-2-(nitroimino)thiazolidine

HRID 379293

Reaction equation

HRID 379293 reaction equation
[N+:1]([N:4]=[C:5]1[NH:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][N:18]=1>C(#N)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:9]2[CH2:8][CH2:7][S:6][C:5]2=[N:4][N+:1]([O-:3])=[O:2])=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 1362474392-Nitroiminothiazolidine

Product 1

HCID 538802633-(2-Chloro-5-pyridylmethyl)-2-(nitroimino)thiazolidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.9 g of 2-nitroiminothiazolidine, 2.9 g of anhydrous potassium carbonate, 3.2 g of 2-chloro-5-pyridylmethylchloride and 50 ml of acetonitrile was refluxed for 5 hours with vigorously stirring. After the reaction, most of the acetonitrile was removed by distillation and water was added to the residue. As the solid product was separated, it was collected by filtration. The crude material was recrystallized from ethanol to give desired 3-(2-chloro-5-pyridylmethyl)-2-(nitroimino)thiazolidine.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customAfter the reaction
  3. custommost of the acetonitrile was removed by distillation and water
  4. additionwas added to the residue
  5. customAs the solid product was separated
  6. filtrationit was collected by filtration
  7. customThe crude material was recrystallized from ethanol

Sources & evidence

ORD record
ord-c5e117cc5b2245c587c08400dffad131
Source dataset
uspto-grants-2001_10
Patent number
US06297374B1

Linked notes

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