2-tert-Butyl-5-(3-methyl-4-nitrophenyl)-1,3,4-oxadiazole → 4-(5-(1,1-Dimethylethyl)-1,3,4-oxadiazol-2-yl)-2-methylaniline

HRID 2121837Notes

Reaction equation

[CH3:1][C:2]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([CH3:19])[CH:11]=2)=[N:8][N:9]=1)([CH3:4])[CH3:3]>[Zn].CN(C)C=O.O>[CH3:4][C:2]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([CH3:19])[CH:11]=2)=[N:8][N:9]=1)([CH3:1])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(1,1-dimethylethyl)-5-(3-methyl-4-nitrophenyl)-1,3,4-oxadiazole (1.6 g), FeCl3.6H2O (5 g) and zinc powder (4 g) in a dimethylformamide/water mixture (1/1, 25 ml) is heated at 100° C. for 30 minutes and then filtered through Celite. After dilution with saturated aqueous sodium carbonate solution, the reaction mixture is extracted with diethyl ether. Drying over magnesium sulphate and evaporation of the organic phase gives the title aniline.

Workup

filtrationfiltered through Celite
extractionAfter dilution with saturated aqueous sodium carbonate solution, the reaction mixture is extracted with diethyl ether
dry with materialDrying over magnesium sulphate and evaporation of the organic phase

Sources & evidence

ORD record: ord-60969689c84e4249a0f45b67a30e7e2d
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696487B2

Reaction notes

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