3-(2-chloro-5-nitrophenyl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one → 3-(5-Amino-2-chlorophenyl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one

HRID 621367Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N:11]1[N:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[O:13][C:12]1=[O:20]>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N:11]2[N:15]=[C:14]([C:16]([CH3:17])([CH3:19])[CH3:18])[O:13][C:12]2=[O:20])[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Electrolytic iron powder (93.5 g) was suspended in 5% acetic acid (187.2 ml), and the suspension was heated to 80° C. A solution of 3-(2-chloro-5-nitrophenyl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one (47.21 g) in acetic acid (167.5 ml) and ethyl acetate (167.5 ml) was added thereto. The resultant mixture was heated at a temperature of 70° C. for 3 hours. The reaction mixture was subjected to filtration on celite while hot. The filtrate was extracted with ethyl acetate, and the extract was washed with water and sodium bicarbonate solution and dried. Removal of the solvent under reduced pressure gave 3-(5-amino-2-chlorophenyl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one (38.28 g). m.p., 126.0° C.

Workup

filtrationThe reaction mixture was subjected to filtration on celite while hot
extractionThe filtrate was extracted with ethyl acetate
washthe extract was washed with water and sodium bicarbonate solution
customdried
customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-06aba9449e18468cae7dc36f2967b89c
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04824465

Reaction notes

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