Nitric Acid → 2-Nitroimino-3-(4-pyridylmethyl)thiazolidine

HRID 376995Notes

Reaction equation

HRID 376995 reaction equation
[NH:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][S:3]1.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[N+:14]([N:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)[CH2:5][CH2:4][S:3]1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 139209202-Imino-3-(4-pyridylmethyl)thiazolidine

Product 1

HCID 543576062-Nitroimino-3-(4-pyridylmethyl)thiazolidine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5.8 g of 2-imino-3-(4-pyridylmethyl)thiazolidine was added to 20 ml of conc. sulfuric acid at -5~0° C. 6 ml of fuming nitric acid was then added dropwise to the solution at the same temperature. After stirring for 30 minutes at 0~5° C., the reaction mixture was poured onto crushed ice. Twice extract with dichloromethan followed by treating in the usual way yielded 1.4 g of desired 2-nitroimino-3-(4-pyridylmethyl)thiazolidine.

Workup

  1. additionthe reaction mixture was poured
  2. customonto crushed ice
  3. extractionTwice extract with dichloromethan
  4. additionby treating in the usual way

Sources & evidence

ORD record
ord-e4d2805be03e4addb9fcdaf05f31692d
Source dataset
uspto-grants-2000_02
Patent number
US06022967

Reaction notes

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