Hydrochloric Acid → 4-[3-(Thiophen-2-yl)-1,2,4-oxadiazol-5-yl]aniline

HRID 462172Notes

Reaction equation

HRID 462172 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.Cl.C([O-])([O-])=O.[K+].[K+]>[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[N:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 7186945-(4-Nitrophenyl)-3-(2-thienyl)-1,2,4-oxadiazole

Product 1

HCID 230082024-[3-(Thiophen-2-yl)-1,2,4-oxadiazol-5-yl]anilineYield 50%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 5-(4-nitrophenyl)-3-(2-thienyl)-1,2,4-oxadiazole (3.1 g, 0.01 mole) in 150 ml of absolute alcohol containing 1.84 ml of concentrated HCl is hydrogenated using 0.4 g of 5% Pd on carbon as catalyst. The solid is slurried with saturated K2CO3 solution and extracted with chloroform. Evaporation of the chloroform in vacuo gives the amine as a yellow solid, 1.4 g (50% yield).

Workup

  1. extractionextracted with chloroform
  2. customEvaporation of the chloroform in vacuo

Sources & evidence

ORD record
ord-214c0041ab6b4e7d9125366fb2bb4d89
Source dataset
uspto-grants-1977_12
Patent number
US04065563

Reaction notes

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