Sodium hydride → 1-(6-Chloro-3-pyridylmethyl)3,3-dimethyl-2-nitroguanidine

HRID 1087102Notes

Reaction equation

HRID 1087102 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:11])[C:5]([NH:7][N+:8]([O-:10])=[O:9])=[NH:6].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][N:14]=1>CN(C=O)C>[Cl:12][C:13]1[N:14]=[CH:15][C:16]([CH2:19][NH:6][C:5]([N:4]([CH3:11])[CH3:3])=[N:7][N+:8]([O-:10])=[O:9])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136047761N,N-Dimethyl-N'-nitroguanidine

Product 1

HCID 1362181971-(6-Chloro-3-pyridylmethyl)3,3-dimethyl-2-nitroguanidineYield 31.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.44g of 60% sodium hydride (in mineral oil) in 10ml of DMF was added 1.32g of N,N-dimethyl-N'-nitroguanidine during 20 minutes at room temperature. After stirring for 10 minutes, 1.62g of 2-chloro-5-(chloromethyl)pyridine was added to the mixture in 5 minutes, and stirred for 2 hours at room temperature and for 4 hours in an oil bath of 60° C. After filtering insoluble materials off, the filtrate was concentrated. The resulting residue was purified by a column chromatography [developing solvent: dichloromethane-ethyl acetate (5:1-3:1)] to obtain 0.82g of 1-(6-chloro-3-pyridylmethyl)-3,3-dimethyl-2nitroguanidine (Compound No. 6).

Workup

  1. stirringstirred for 2 hours at room temperature and for 4 hours in an oil bath of 60° C
  2. filtrationAfter filtering insoluble materials off, the filtrate
  3. concentrationwas concentrated
  4. customThe resulting residue was purified by a column chromatography [developing solvent: dichloromethane-ethyl acetate (5:1-3:1)]

Sources & evidence

ORD record
ord-e3a2ee252aa446378b25eccafe0566c4
Source dataset
uspto-grants-1991_07
Patent number
US05034404

Reaction notes

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