Hydrochloric Acid → HCID 136169378, compound

HRID 1475145Notes

Reaction equation

HRID 1475145 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[NH:12][C:11]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#N)=[CH:17][CH:16]=3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(C1C=CC(C(=O)C(O)=[O:33])=CC=1)#N.Cl.ClC1C=C(NN)C=CC=1Cl.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[NH:12][C:11]([C:15]3[CH:22]=[CH:21][C:18]([CH:19]=[O:33])=[CH:17][CH:16]=3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 582549HCID 582549, compoundHCID 3084323(3,4-Dichlorophenyl)hydrazine monohydrochlorideHCID 136353458HCID 136353458, compound

Product 1

HCID 136169378HCID 136169378, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[1-(3,4-Dichloro-phenyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-benzonitrile. A suspension of 4-cyanophenyl-oxo-acetic acid (100 mg, 0.571 mmol), (3,4-dichlorophenyl)hydrazine hydrochloride (122 mg, 0.571 mmol), 12.1 N HCl (5 uL, 0.057 mmol), and H2O (˜10 mL) in a 25 mL reaction vial was stirred vigorously at ambient temperature for 24 h. The hydrazone was obtained by vacuum filtration and placed into a 100 mL round bottom flask with a magnetic stir bar. The flask was then supplemented with triethylamine (0.08 mL, 0.571 mmol), diphenylphosphoryl azide (157 mg, 0.571 mmol), and toluene (20 mL) before heating at 110° C. for 1 h. Upon cooling the contents were quenched with 10% NaOH (aq) and made acidic (pH 1) with conc. HCl. Precipitation was allowed for 15 min before the intermediate was obtained by vacuum filtration and dried overnight in a 45° C. vacuum oven (16 mg, 8%). The nitrile was reduced to the aldehyde using DIBAL under conditions previously described.

Workup

  1. customin a 25 mL reaction vial

Sources & evidence

ORD record
ord-ed25cab0aa924616a401ef214c0779bc
Source dataset
uspto-grants-2015_04
Patent number
US09018363B2

Reaction notes

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