Acetonitrile → HCID 178509164, compound
Reaction equation
[N:1]1([CH:7]=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CSC(SC)=[N:12][C:13]#[N:14].O.[NH2:18]N.[C:20](#[N:22])C>>[NH2:12][C:13]1[NH:14][C:20]([N:4]2[CH2:5][CH2:6][N:1]([CH:7]=[O:8])[CH2:2][CH2:3]2)=[N:22][N:18]=1Participants
Procedure
A mixture of 11.4 g (0.1 mole) of piperazinecarboxaldehyde, 14.6 g (0.1 mole) of dimethyl cyanodithioiminocarbonate and 150 ml of acetonitrile was heated at reflux for 18 hours, the evolved gas being led into a sodium hypochlorite trap. The reaction mixture was cooled and filtered to remove a small amount of colorless solid. The filter was washed with acetonitrile, the wash being added to the filtrate. Then 5.5 ml (0.11 mole) of hydrazine hydrate was added to the filtrate and the mixture was refluxed for 4 hours, again with a sodium hypochlorite trap installed. Crystals appeared during reflux. The mixture was cooled and filtered. The material was washed with acetonitrile and gave 17.8 g of the product of the Example, mp 150°-151° C. (dec.).
Workup
- temperaturewas heated
- temperatureat reflux for 18 hours
- customthe evolved gas being led into a sodium hypochlorite trap
- temperatureThe reaction mixture was cooled
- filtrationfiltered
- customto remove a small amount of colorless solid
- washThe filter was washed with acetonitrile
- additionthe wash being added to the filtrate
- temperaturethe mixture was refluxed for 4 hours, again with a sodium hypochlorite trap
- temperatureduring reflux
- temperatureThe mixture was cooled
- filtrationfiltered
- washThe material was washed with acetonitrile
Sources & evidence
- ORD record
- ord-ffb8f11e86154a6798a3a99f64ae0f91
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04582833
Reaction notes
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