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

HRID 257726Notes

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, Example 153 of Table 1.

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-eccb4315a34a4fb7880e48bacee71aa9
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05264415

Reaction notes

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