Sodium hydride → HCID 136378387, compound

HRID 1463830Notes

Reaction equation

HRID 1463830 reaction equation
[H-].[Na+].[N+:3]([N:6]=[C:7]1[NH:11][CH2:10][CH2:9][NH:8]1)([O-:5])=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][N+:14]=1[O-:21]>C(#N)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:8]2[CH2:9][CH2:10][NH:11][C:7]2=[N:6][N+:3]([O-:5])=[O:4])=[CH:15][N+:14]=1[O-:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 124874662-Chloro-5-chloromethylpyridine 1-oxideHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 136378387HCID 136378387, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

0.85 g of a 55% sodium hydride dispersion in mineral oil is added in portions to a solution of 2.7 g of 2-nitroimino-imidazolidine in 70 ml of acetonitrile. The mixture is stirred for 1.5 hours under a nitrogen atmosphere, and then 3.72 g of 2-chloro-5-chloromethyl-pyridine-N-oxide are added in portions. The reaction mixture is stirred at room temperature for 16 hours and then filtered. The crude product is crystallised out by cooling the filtrate to 0° C. The product is separated off and washed with diethyl ether, yielding pure 2-chloro-5-(2-nitroimino-imidazolidin-1-yl-methyl)-pyridine-N-oxide, m.p. 200° C. (with decomposition).

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 16 hours
  2. filtrationfiltered
  3. customThe crude product is crystallised out
  4. customThe product is separated off
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c5855fc5338e4aadb7c5d4d91e7d7275
Source dataset
uspto-grants-1994_04
Patent number
US05302605

Reaction notes

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