Sodium Diethyldithiocarbamate → 2-Amino-5-cyano-6-diethylthiocarbamylthio-1-n-octyl-4-n-octylamino pyridinium chloride

HRID 267735

Reaction equation

HRID 267735 reaction equation
[Cl-].[NH2:2][C:3]1[CH:8]=[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:6]([C:18]#[N:19])=[C:5]([Cl:20])[N+:4]=1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[CH2:29]([N:31]([CH2:35][CH3:36])[C:32](=[S:34])[S-:33])[CH3:30].[Na+]>CN(C)C=O>[Cl-:20].[NH2:2][C:3]1[CH:8]=[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:6]([C:18]#[N:19])=[C:5]([S:34][C:32](=[S:33])[N:31]([CH2:35][CH3:36])[CH2:29][CH3:30])[N+:4]=1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 533728Sodium DiethyldithiocarbamateHCID 122967422-Amino-6-chloro-5-cyano-1-n-octyl-4-n-octylamino pyridinium chloride

Product 1

HCID 867331562-Amino-5-cyano-6-diethylthiocarbamylthio-1-n-octyl-4-n-octylamino pyridinium chlorideYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.5 gms (.01 mole) of 2-amino-6-chloro-5-cyano-1-n-octyl-4-n-octylamino pyridinium chloride (compound 14 - Table 1) was dissolved in dimethylformamide and 2.2 gms (0.01 mole) of sodium diethyldithiocarbamate added and the solution refluxed for 60 minutes. This was then cooled, filtered and the solvent evaporated off. Methanol was added and 1.6 gms (30% yield) of 2-amino-5-cyano-6-diethylthiocarbamylthio-1-n-octyl-4-n-octylamino pyridinium chloride (compound 80 - Table 5) was filtered off and recrystallised from methanol (MPt 124° - 126°C.)

Workup

  1. temperaturethe solution refluxed for 60 minutes
  2. temperatureThis was then cooled
  3. filtrationfiltered
  4. customthe solvent evaporated off
  5. additionMethanol was added

Sources & evidence

ORD record
ord-1c92f00fecb54eda8c52435663db76a2
Source dataset
uspto-grants-1976_03
Patent number
US03944557

Linked notes

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