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

HRID 1252132Notes

Reaction equation

HRID 1252132 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-632a40e3951b44d9b72466856cfc8465
Source dataset
uspto-grants-1988_05
Patent number
US04742060

Reaction notes

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