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

HRID 376993Notes

Reaction equation

HRID 376993 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 5 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 5 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-3662f40537e848e098536adb89767ee4
Source dataset
uspto-grants-2000_02
Patent number
US06022967

Reaction notes

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