Sodium Hydroxide → 4-Chlorophenyl-2-[(1,2,4-triazol-1-yl)methyl]butyramide

HRID 2211087Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:17][CH3:18])([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C:9]#[N:10])=[CH:4][CH:3]=1.[OH-:19].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)([CH2:17][CH3:18])[C:9]([NH2:10])=[O:19])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 500 mL flask was charged 100.0 g (0.38 mole) of alpha-(4-chlorophenyl)alpha-ethyl-1H-1,2,4-triazole-1-propanenitrile and 100 mL of dimethyl sulfoxide. To the stirring solution was added 100 g (1.25 mole) of 50% sodium hydroxide. The reaction mixture was heated at 100° C. for 1 hour after which GLC indicated the starting material was consumed. The reaction was poured into water and extracted with ethyl acetate. After washing with brine, the organic phase was dried over magnesium sulfate and concentrated under vacuum without heating. Removal of the solvent gave a foamy glassy solid which was triturated with hexane, filtered and gave 97 g (91% yield) of a white solid, melting point 139°-140° C.

Workup

customwas consumed
additionThe reaction was poured into water
extractionextracted with ethyl acetate
washAfter washing with brine
dry with materialthe organic phase was dried over magnesium sulfate
concentrationconcentrated under vacuum
temperaturewithout heating
customRemoval of the solvent
customgave a foamy glassy solid which
customwas triturated with hexane
filtrationfiltered

Sources & evidence

ORD record: ord-4f625ba3cb574b149a17b270c17121b3
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05462931

Reaction notes

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