1,1-Ethenediamine, N-[(6-chloro-3-pyridinyl)methyl]-N'-methyl-2-nitro- → 1(6-Chloro-3-pyridylmethyl)amino-1-methylamino-2-methanesulfonylthiocarbamoyl-2-nitroethylene

HRID 1457913Notes

Reaction equation

HRID 1457913 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([NH:15][CH3:16])=[CH:11][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[CH3:17][S:18]([N:21]=[C:22]=[S:23])(=[O:20])=[O:19]>CC#N>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([NH:15][CH3:16])=[C:11]([C:22](=[S:23])[NH:21][S:18]([CH3:17])(=[O:20])=[O:19])[N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 43256191,1-Ethenediamine, N-[(6-chloro-3-pyridinyl)methyl]-N'-methyl-2-nitro-HCID 12297546Methanesulfonyl isothiocyanate

Product 1

HCID 598966301(6-Chloro-3-pyridylmethyl)amino-1-methylamino-2-methanesulfonylthiocarbamoyl-2-nitroethyleneYield 32.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 50 ml of CH3CN was dissolved 0.50 g (0.002 mole) of 1-(6-chloro-3-pyridylmethyl)amino-1-methylamino-2-nitroethylene, followed by addition of 0.30 g (0.002 mole) of methanesulfonyl isothiocyanate. The mixture was stirred at room temperature for 2 hours. The CH3CN was distilled off and the residue was purified by silica gel column chromatography. The procedure gave 0.25 g of the title compound as yellow crystals.

Workup

  1. distillationThe CH3CN was distilled off
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5654b257adbf41689831214f22e343c9
Source dataset
uspto-grants-1998_12
Patent number
US05849768

Reaction notes

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