p-Toluenesulfonic acid → HCID 178456629, compound

HRID 915014Notes

Reaction equation

[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11](=O)[CH:12]=[N:13][OH:14])=[N:5]1)([CH3:3])[CH3:2].[NH2:16][CH:17]([C:20]#[N:21])[C:18]#[N:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CC(O)C.CCOC(C)=O.O>[NH2:21][C:20]1[C:17]([C:18]#[N:19])=[N:16][C:11]([C:6]2[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)=[CH:12][N+:13]=1[O-:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl) (oxo)acetaldehyde oxime (11.16 g), aminomalononitrile (13.6 g) and p-toluenesulfonic acid (10.2 g) in 2-propanol (200 ml) was stirred at 50° C. for 3 hours. Water, aq. NaHCO3 and EtOAc were added to the reaction mixture to give a pale yellow precipitate. The precipitate was collected by filtration to obtain 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarbonitrile 4-oxide (3.84 g) as white powder.

Workup

customto give a pale yellow precipitate
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-ce5bbd6703154f7a809c9d25a9e25b85
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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