2-Aminothiophenol → Benzenamine, 2-((1,2,4-oxadiazol-3-ylmethyl)thio)-

HRID 848170Notes

Reaction equation

HRID 848170 reaction equation
[Na].[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].Cl[CH2:11][C:12]1[N:16]=[CH:15][O:14][N:13]=1>C(O)C>[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:11][C:12]1[N:16]=[CH:15][O:14][N:13]=1

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 27357653-(Chloromethyl)-1,2,4-oxadiazoleHCID 5360545Sodium

Product 1

HCID 3057622Benzenamine, 2-((1,2,4-oxadiazol-3-ylmethyl)thio)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (1.27 g; 0.055 mol) was dissolved in absolute ethanol (50 ml) and to this was added 2-aminothiophenol (7.38 g; 0.059 mol). To the resulting solution was added 3-chloromethyl-1,2,4-oxadiazole (6.59 g; 0.055 mol) dropwise over 10 minutes. The resulting mixture was then stirred at ambient temperature for 30 minutes, sodium chloride removed by filtration and the filtrate was evaporated to dryness under reduced pressure to give 3-(2-aminophenylthiomethyl)-1,2,4-oxadiazole which was re-crystallised from isopropanol; m.p. 57°.

Workup

  1. customsodium chloride removed by filtration
  2. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8a42b7c4c1d94c35863f966d25765d11
Source dataset
uspto-grants-1981_10
Patent number
US04294843

Reaction notes

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