Benzonitrile → 2-(3-Phenyl-1,2,4-oxadiazol-5-yl)aniline

HRID 1030302Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.O[NH3+:13].O[NH3+].[C:16]12[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:21]C(=O)[O:19][C:17]2=O.[OH-].[Na+].[C:30](#[N:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O.C(O)C(C)C>[C:31]1([C:30]2[N:13]=[C:17]([C:16]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH2:21])[O:19][N:37]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of 151 g of sodium carbonate in 650 ml of water at room temperature were added in succession 650 ml of isobutanol, 268 g of benzonitrile and, a little at a time, 220 g of hydroxylammonium sulfate The mixture was then heated to 90° C. and stirred at that temperature for five hours It was then cooled back to 30-40° C. and 392 g of isatoic anhydride were added a little at a time at that temperature. The reaction mixture was then heated back up to 80° C. and 100 g of 50% strength by weight sodium hydroxide solution were added dropwise. The isobutanol was then distilled off quantitatively by introducing steam, and the coarsely crystalline residue was filtered off with suction, washed with water and dried, leaving 470 g of 2-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline in a coarsely crystalline form.

Workup

temperatureThe reaction mixture was then heated back up to 80° C.
distillationThe isobutanol was then distilled off quantitatively
additionby introducing steam
filtrationthe coarsely crystalline residue was filtered off with suction
washwashed with water
customdried

Sources & evidence

ORD record: ord-aeb7e9a435754bc48b8270c31a006a8b
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05104991

Reaction notes

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