Phosphorus oxychloride → HCID 178509740, compound

HRID 452683Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1H-benzotriazole-5-carbohydrazide (354 mg, 2.00 mmol), 3-(3-cyanophenyl)propionic acid (350 mg, 2.00 mmol) and phosphorus oxychloride (5 mL) was stirred at 100° C. for 4 hr. After cooling, the reaction mixture was poured into water and neutralized with sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and recrystallized from methanol/water to give the title compound (104 mg, yield 16%) as colorless crystals.

Workup

temperatureAfter cooling
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate)
customrecrystallized from methanol/water

Sources & evidence

ORD record: ord-6cc29173eb2d432fb8b64fa6719b8c8c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492378B2

Reaction notes

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