Phosphorus oxychloride → HCID 68663808, compound

HRID 452610Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[N+:20]([O-:22])=[O:21])[C:13]([NH:15][NH2:16])=[O:14])=[CH:5][CH:4]=1.[F:23][C:24]1[CH:25]=[C:26]([CH2:30][CH2:31][C:32](O)=O)[CH:27]=[CH:28][CH:29]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>>[F:23][C:24]1[CH:25]=[C:26]([CH2:30][CH2:31][C:32]2[O:14][C:13]([C:12]3[CH:17]=[CH:18][C:19]([N+:20]([O-:22])=[O:21])=[C:10]([CH:11]=3)[NH:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[N:15][N:16]=2)[CH:27]=[CH:28][CH:29]=1

Participants

Reactant 4

HCID 24813Phosphorus oxychloride

HCID 516892Sodium Bicarbonate

HCID 27374893-(3-Fluorophenyl)propionic acid

HCID 68663380HCID 68663380, compound

Product 1

HCID 68663808HCID 68663808, compoundYield 69%

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-[(4-methoxyphenyl)amino]-4-nitrobenzohydrazide (1.60 g, 5.29 mmol), 3-(3-fluorophenyl)propionic acid (0.89 g, 5.29 mmol) and phosphorus oxychloride (5.29 mL) was stirred at 100° C. for 2 hr. The reaction mixture was cooled to 0° C., neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=3/1) to give the title compound (1.51 g, yield 69%) as orange crystals.

Workup

temperatureThe reaction mixture was cooled to 0° C.
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-0fb9fbefbca142c0bdd18cb622ebc4a1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492378B2

Reaction notes

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