Triethylamine → 5-(4-Isothiocyanophenyl)-3-(2-thienyl)-1,2,4-oxadiazole

HRID 2397863Notes

Reaction equation

HRID 2397863 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25](Cl)(Cl)=[S:26]>O1CCCC1>[N:1]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[N:9]=2)=[CH:4][CH:3]=1)=[C:25]=[S:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 230082024-[3-(Thiophen-2-yl)-1,2,4-oxadiazol-5-yl]aniline

Product 1

HCID 213907005-(4-Isothiocyanophenyl)-3-(2-thienyl)-1,2,4-oxadiazoleYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.2 g (0.005 mole) of 5-(4-aminophenyl)-3-(2-thienyl)-1,2,4-oxadiazole in 150 ml of dry tetrahydrofuran containing 0.49 g of triethylamine, 0.56 g (0.005 mole) of thiophosgene is added and the mixture stirred at room temperature for 3 hours. After filtration, the solution is evaporated in vacuo to give the crude product. It is crystallized from petroleum ether to give 0.7 g (50%) of the title compound, m.p. 161°-162° .

Workup

  1. filtrationAfter filtration
  2. customthe solution is evaporated in vacuo
  3. customto give the crude product
  4. customIt is crystallized from petroleum ether

Sources & evidence

ORD record
ord-c177657a47b344f2b5e34c62676edad0
Source dataset
uspto-grants-1977_05
Patent number
US04022901

Reaction notes

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