1,1-Bis(methylthio)-2-nitroethylene → 1-(2-Chloro-5-pyridylmethyl)4-methyl-2-(nitromethylene)imidazolidine

HRID 22215

Reaction equation

HRID 22215 reaction equation
[NH2:1][CH:2]([CH3:13])[CH2:3][NH:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[N:10][CH:11]=1.[N+:14]([CH:17]=[C:18](SC)SC)([O-:16])=[O:15]>CO>[Cl:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][N:4]2[CH2:3][CH:2]([CH3:13])[NH:1][C:18]2=[CH:17][N+:14]([O-:16])=[O:15])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 139209182-Amino-1-(2-chloro-5-pyridylmethylamino)propane

Product 1

HCID 867421431-(2-Chloro-5-pyridylmethyl)4-methyl-2-(nitromethylene)imidazolidineYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2 g of 2-amino-1-(2-chloro-5-pyridylmethylamino)propane, 1.6 g of 1-nitro-2,2-bis(methylthio)ethylene and 20 ml of methanol was refluxed for hours with stirring. A crystaline product was precipitated after standing at room temperature. The product was filtered with suction, washed with methanol and then dried in vacuum. 1.9 g of 1-(2-chloro-5-pyridylmethyl)-4-methyl-2-(nitromethylene)imidazolidine was obtained in form of light yellow crystals.

Workup

  1. temperaturewas refluxed for hours
  2. customA crystaline product was precipitated
  3. customafter standing at room temperature
  4. filtrationThe product was filtered with suction
  5. washwashed with methanol
  6. customdried in vacuum

Sources & evidence

ORD record
ord-1bd1791614cd400c8e7f793356fce6e3
Source dataset
uspto-grants-1995_06
Patent number
US05428032

Linked notes

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