Triethylamine → HCID 178502659, compound

HRID 2187235Notes

Reaction equation

HRID 2187235 reaction equation
CS[C:3]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[CH:4][N+:5]([O-:7])=[O:6].[CH3:16][O:17][NH3+:18].[Cl-].C(N(CC)CC)C>C(O)C(C)C>[CH3:16][O:17][N:18]=[C:3]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:4][N+:5]([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11639O-methylhydroxylammonium chlorideHCID 70155832HCID 70155832, compound

Product 1

HCID 178502659HCID 178502659, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent2×

Procedure

To 3 ml of isobutyl alcohol was added 0.75 g (0.0033 mole) of 1-methylthio-1-(3-pyridylmethyl)amino-2-nitroethylene, followed by addition of 0.56 g of 0-methylhydroxylamine hydrochloride at 100-110° C. Then, a solution of 0.93 ml of triethylamine in 1 ml of isobutyl alcohol was added dropwise at the same temperature with stirring over a period of 30 minutes. After completion of dropwise addition, the reaction mixture was allowed to cool to room temperature and the solvent was distilled off. The residue was purified by silica gel column chromatography [eluents: MeOH—CHCl3 (1:3) in the first run and MeOH—CHCl3 (1:10) in the second run] to give 0.23 g of the title compound as yellow crystals.

Workup

  1. additionAfter completion of dropwise addition
  2. distillationthe solvent was distilled off
  3. customThe residue was purified by silica gel column chromatography [eluents

Sources & evidence

ORD record
ord-8471605050ac46ec9b29b3d11b907ee3
Source dataset
uspto-grants-2002_06
Patent number
US06407248B1

Reaction notes

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