Phosphorus oxychloride → 3-Chloro-5-phenyl-pyridazine-4-carbonitrile

Reaction equation

O=[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[N:4][NH:3]1.P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:2]1[N:3]=[N:4][CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]=1[C:8]#[N:9]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 597350963-Oxo-5-phenyl-2,3-dihydro-pyridazine-4-carbonitrile

Product 1

HCID 597350973-Chloro-5-phenyl-pyridazine-4-carbonitrile

Conditions

Temperature: 100 °C

Procedure

3-Oxo-5-phenyl-2,3-dihydro-pyridazine-4-carbonitrile (70 mg) was suspended in 1 mL phosphorous oxychloride and heated to 100° C. for 6 hours. The mixture was then cooled and poured onto ice. The resulting brown solid product was filtered and air dried and used in the next step without further purification.

Workup

temperatureThe mixture was then cooled
additionpoured onto ice
filtrationThe resulting brown solid product was filtered
customair dried
customused in the next step without further purification

Sources & evidence

ORD record: ord-bd5e34d29f394ea2bd540100a0cf9937
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666647B2

Reaction notes

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