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

HRID 359510Notes

Reaction equation

HRID 359510 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 crystalline 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 crystalline 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-a3232ecf81784d0daa18166bb7bd5a80
Source dataset
uspto-grants-1991_03
Patent number
US05001138

Reaction notes

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