3,4-Diaminopyridine → HCID 178503896, compound

HRID 257423

Reaction equation

HRID 257423 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:9][S:10][C:11](SC)=[N:12][C:13]#[N:14]>N1C=CC=CC=1>[CH3:9][S:10][C:11](=[N:12][C:13]#[N:14])[NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 2

HCID 59183,4-DiaminopyridineHCID 66289Dimethyl N-cyanodithioiminocarbonate

Product 1

HCID 178503896HCID 178503896, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4-Diaminopyridine (4 g, 36.6 mmol) was suspended in anhydrous pyridine (100 ml), and S,S'-dimethyl N-cyanodithioiminocarbonate (8.0 g, 55.0 mmol) was added thereto. The mixture was stirred at room temperature for 4 days. The resulting powder was collected from the reaction mixture by filtration, and washed with ether (100 ml) to obtain crude crystals. The crystals were purified by recrystallization from methanol-ether to obtain 1.91 g of the intended product as a white powder (yield: 58%). On the other hand, the filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, eluent: chloroform:methanol=4:1 (v/v)) to obtain 2.8 g of the intended product (total yield: 95%).

Workup

  1. filtrationThe resulting powder was collected from the reaction mixture by filtration
  2. washwashed with ether (100 ml)
  3. customto obtain crude crystals
  4. customThe crystals were purified by recrystallization from methanol-ether

Sources & evidence

ORD record
ord-9cb7892e7c7344dfae5c4dd0d1699a69
Source dataset
uspto-grants-1993_11
Patent number
US05262415

Linked notes

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