Stannous chloride dihydrate → 3-(4-Aminophenyl)-1,2,4-oxadiazol-5(2H)-one

HRID 56606Notes

Reaction equation

O.O.[Sn](Cl)Cl.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:19][C:18](=[O:20])[O:17][N:16]=2)=[CH:11][CH:10]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:6][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[NH:19][C:18](=[O:20])[O:17][N:16]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

6.5 g (29 mmol, 4 eq.) of tin(II) chloride dihydrate were added to a solution of 1.5 g (7.2 mmol) of 3-(4-nitrophenyl)-1,2,4-oxadiazol-5(4H)-one in 75 ml of ethanol, and the mixture was stirred at 70° C. for 1 h. The reaction mixture was poured into ice-water, and sodium bicarbonate was added carefully until a pH of 8 had been reached. The mixture was filtered through a filter layer and the residue was washed with ethyl acetate. The combined filtrates were concentrated under reduced pressure. The residue was stirred with dichloromethane and methanol, treated in an ultrasonic bath for 10 min and then filtered. The filtrate was concentrated under reduced pressure and dried. Yield: 1.4 g (quant.)

Workup

additionwas added carefully until a pH of 8
filtrationThe mixture was filtered through a filter layer
washthe residue was washed with ethyl acetate
concentrationThe combined filtrates were concentrated under reduced pressure
stirringThe residue was stirred with dichloromethane and methanol
additiontreated in an ultrasonic bath for 10 min
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customdried

Sources & evidence

ORD record: ord-5f72e1b89c4b47f1bf9a1b73b7943261
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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