Water → 4,5-Dihydro-4-oxo-1,3-dithiolo (4,5-d)-pyridazine-2-ylidene-propanedinitrile

HRID 25935Notes

Reaction equation

HRID 25935 reaction equation
[SH:1][C:2](=[C:4]([C:7]#[N:8])[C:5]#[N:6])[SH:3].[Na].[Na].O.C[N:13]([CH:15]=[O:16])C>>[O:16]=[C:15]1[NH:13][N:6]=[CH:5][C:4]2[S:1][C:2](=[C:4]([C:7]#[N:8])[C:5]#[N:6])[S:3][C:2]1=2

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 86735117Disodium dimercaptomethylenemalononitrile

Product 1

HCID 189912934,5-Dihydro-4-oxo-1,3-dithiolo (4,5-d)-pyridazine-2-ylidene-propanedinitrileYield 90%

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 20 g (0.1 mole) disodiumdimercaptomethylene malononitrile dissolved in 250 ml of DMF was added 16.5 g (0.1 mole) of 4,5-dichloro-3-pyridiazone. The reaction mixture was stirred at room temperature (approximately 20° C.) for 0.25 hours and was thereafter poured with stirring into 1 liter of water. The resulting mixture was allowed to stand for four hours during which time a yellow-gray precipitate slowly formed. This precipitate was separated by filtration, washed with water, and dried in vacuo to yield 21.1 g (90% yield from the pyridiazone) of a yellow-gray solid, m.p. (decomposition) 310°-340° C.

Workup

  1. additionwas added 16.5 g (0.1 mole) of 4,5-dichloro-3-pyridiazone
  2. additionwas thereafter poured
  3. waitto stand for four hours during which time
  4. customa yellow-gray precipitate slowly formed
  5. customThis precipitate was separated by filtration
  6. washwashed with water
  7. customdried in vacuo
  8. customto yield 21.1 g (90% yield from the pyridiazone) of a yellow-gray solid, m.p. (decomposition) 310°-340° C.

Sources & evidence

ORD record
ord-99600fb47d3a49ecb0cdc24f0efcf210
Source dataset
uspto-grants-1979_04
Patent number
US04147784

Reaction notes

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