Phosphorus oxychloride → HCID 12992133, compound
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:11][C:10](=O)[C:9]([C:13]#[N:14])=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:10]1[C:9]([C:13]#[N:14])=[CH:8][C:7]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[N:11]=1Participants
Conditions
- Temperature
- 110 °C
Procedure
A suspension of 6-(2-furyl)-2-oxo-5-(4-pyridyl)-1,2-dihydro-3-pyridinecarbonitrile (21.0 g, 79.8 mmol) in phosphorus oxychloride (90 g) was stirred in a nitrogen atmosphere at 110° C. After 4 hours, additional phosphorus oxychloride (50 g) was added thereto, followed by heating under stirring for further 5 hours. After cooling as it was, the reaction solution was concentrated. After ice was added to the residue, it was neutralized with saturated sodium bicarbonate. After extracting with ethyl acetate (2 1)-tetrahydrofuran (1 1), the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. After adding diethyl ether to the residue, the resulting solid was collected by filtration and washed with diethyl ether, to give the title compound (13.6 g, 61%) as a dark yellow solid.
Workup
- temperatureby heating
- stirringunder stirring for further 5 hours
- temperatureAfter cooling as it
- concentrationthe reaction solution was concentrated
- additionAfter ice was added to the residue, it
- extractionAfter extracting with ethyl acetate (2 1)-tetrahydrofuran (1 1)
- washthe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- additionAfter adding diethyl ether to the residue
- filtrationthe resulting solid was collected by filtration
- washwashed with diethyl ether
Sources & evidence
- ORD record
- ord-29a8008abd954c31bf1c530b1c0d44a8
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06750232B2
Reaction notes
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