Water → HCID 20566329, compound

HRID 856641Notes

Reaction equation

HRID 856641 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl[CH2:10][C:11]1[N:15]=[CH:14][O:13][N:12]=1.C(N(CC)CC)C.O>C1COCC1>[O:13]1[CH:14]=[N:15][C:11]([CH2:10][S:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)=[N:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 145104-AminothiophenolHCID 27357653-(Chloromethyl)-1,2,4-oxadiazole

Product 1

HCID 20566329HCID 20566329, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-aminothiophenol (1.0 g), 3-chloromethyl-1,2,4-oxadiazole (1.0 g) and triethylamine (1.1 ml) in THF (10 ml) was stirred at room temperature for 18 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:3→1:2), to give 4-(1,2,4-oxadiazol-3-ylmethylthio)aniline (1.36 g) as pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained residue was separated
  6. custompurified by column chromatography (ethyl acetate:hexane 1:3→1:2)

Sources & evidence

ORD record
ord-0bb0c17240cf4fcea6b511d072619666
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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