Phosphorus oxychloride → HCID 14621183, compound

HRID 1111062Notes

Reaction equation

[CH2:1]([C:4]1[C:5](=O)[C:6]([C:12]([NH:14][C:15]2[C:20]([CH2:21][CH3:22])=[CH:19][C:18]([CH3:23])=[CH:17][C:16]=2[CH2:24][CH3:25])=[O:13])=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])[CH:2]=[CH2:3].P(Cl)(Cl)([Cl:29])=O>>[CH2:1]([C:4]1[C:5]([Cl:29])=[C:6]([C:12]([NH:14][C:15]2[C:20]([CH2:21][CH3:22])=[CH:19][C:18]([CH3:23])=[CH:17][C:16]=2[CH2:24][CH3:25])=[O:13])[C:7]([CH3:11])=[N:8][C:9]=1[CH3:10])[CH:2]=[CH2:3]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 14621182HCID 14621182, compound

Product 1

HCID 14621183HCID 14621183, compound

Procedure

A mixture of 0.85 g (2.41 m mol) of 5-allyl-N-(2,6-diethyl-4-methylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide and 5 ml of phosphorus oxychloride was heated under reflux for an hour. An excess of phosphorus oxychloxide was removed under vacuum, and the residue was dissolved in 100 ml of methylene chloride. Then the resulting solution was added into 150 ml of saturated sodium bicarbonate solution, followed by stirring for an hour at room temperature. The organic layer was washed with water, dried and concentrated by the conventional method. The resultant crystalline residue was recrystallized from ethyl acetate to give 0.84 g of the title compound, m.p. 192.5°-194° C.

Workup

temperaturewas heated
temperatureunder reflux for an hour
customAn excess of phosphorus oxychloxide was removed under vacuum
dissolutionthe residue was dissolved in 100 ml of methylene chloride
additionThen the resulting solution was added into 150 ml of saturated sodium bicarbonate solution
washThe organic layer was washed with water
customdried
concentrationconcentrated by the conventional method
customThe resultant crystalline residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-b5d48606eb3d42f182ce85be507ec11e
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04978385

Reaction notes

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