N-((6-chloro-3-pyridinyl)methyl)-1,2-ethane-diamine → HCID 72727592, compound

HRID 1382227Notes

Reaction equation

HRID 1382227 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][NH2:12])=[CH:4][N:3]=1.[N+:13]([CH2:16][C:17](SC)=[S:18])([O-:15])=[O:14]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:17]([SH:18])=[CH:16][N+:13]([O-:15])=[O:14])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 10997737N-((6-chloro-3-pyridinyl)methyl)-1,2-ethane-diamineHCID 14653529HCID 14653529, compound

Product 1

HCID 72727592HCID 72727592, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

N-(2-chloro-5-pyridylmethyl)ethylenediamine (2.0 g) and methyl 2-nitrodithioacetate (1.7 g) were dissolved in methanol (40 ml), and the solution was heated at 50° C. for 1 hour in a stream of nitrogen. The solution was cooled to room temperature whereupon crystals were precipitated. The crystals were collected by filtration, washed with a small amount of methanol, and then dried to give the desired N-(2-chloro-5-pyridylmethyl)-N'-(1-mercapto-2-nitrovinyl)ethylenediamine (1.2 g) having a melting point of 136° to 137° C. (decomp.).

Workup

  1. temperatureThe solution was cooled to room temperature whereupon crystals
  2. customwere precipitated
  3. filtrationThe crystals were collected by filtration
  4. washwashed with a small amount of methanol
  5. customdried

Sources & evidence

ORD record
ord-26ca90fa4e254a2998a2105bd18d18e5
Source dataset
uspto-grants-1989_02
Patent number
US04806553

Reaction notes

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