Acetonitrile → 1-(2-Fluoro-5-pyridylmethyl) 2-(nitroimino)imidazolidine

HRID 2211033Notes

Reaction equation

HRID 2211033 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][N:3]=1.[N+:10]([N:13]=[C:14]1[NH:18][CH2:17][CH2:16][NH:15]1)([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:15]2[CH2:16][CH2:17][NH:18][C:14]2=[N:13][N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 220506385-(Bromomethyl)-2-fluoropyridineHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 1363427881-(2-Fluoro-5-pyridylmethyl) 2-(nitroimino)imidazolidineYield 50.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-fluoro-5-pyridylmethyl bromide (9.5 g), 2-(nitroimino)imidazolidine (6.5 g), potassium carbonate (7.6 g) and acetonitrile (100 ml) was refluxed for 2 hours with stirring. After the reaction, the reaction mixture was cooled to room temperature, and cold water (100 ml) was added. The resulting crystals were collected by filtration and washed with ether to give slightly colored 1-(2-fluoro-5-pyridylmethyl)-2-(nitroimino)imidazolidine (6.0 g) as the desired compound. mp. 121°-124° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter the reaction
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with ether

Sources & evidence

ORD record
ord-1efa67cadc854543a02d365a14b5f506
Source dataset
uspto-grants-1995_10
Patent number
US05461167

Reaction notes

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