Water → N-(2-chloro-5-pyridylmethyl)-N-methyl-N'-(1-benzylthio-2-nitrovinyl)ethylenediamine

HRID 1382230Notes

Reaction equation

HRID 1382230 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:13]([SH:18])=[CH:14][N+:15]([O-:17])=[O:16])=[CH:4][N:3]=1.[C:19](=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:19])[CH2:10][CH2:11][NH:12][C:13]([S:18][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:14][N+:15]([O-:17])=[O:16])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 72727592HCID 72727592, compound

Product 1

HCID 86742750N-(2-chloro-5-pyridylmethyl)-N-methyl-N'-(1-benzylthio-2-nitrovinyl)ethylenediamineYield 15.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound synthesized in Example 2 (1.4 g) was dissolved in dry acetonitrile (30 ml), and potassium carbonate (1.4 g) was added. The mixture was stirred at room temperature for 30 minutes. Then, benzyl bromide (0.9 g) was added, and the mixture was heated at 50° C. for 2 hours with stirring. The reaction mixture was cooled to room temperature, and poured into water for neutralization. The aqueous layer was extracted with dichloromethane. The crude product was purified by silica gel column chromatography to give the desired N-(2-chloro-5-pyridylmethyl)-N-methyl-N'-(1-benzylthio-2-nitrovinyl)ethylenediamine (0.3 g) having a melting point of 119° to 123° C.

Workup

  1. temperaturethe mixture was heated at 50° C. for 2 hours
  2. stirringwith stirring
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2db12852ffe449e7b7f82fe3549b03ab
Source dataset
uspto-grants-1989_02
Patent number
US04806553

Reaction notes

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