Potassium Carbonate → 5-[(4-Aminophenoxy)methyl]-3-phenyl-1,2,4-oxadiazole

HRID 1474814Notes

Reaction equation

HRID 1474814 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[NH2:1][C:4]1[CH:22]=[CH:21][C:7]([O:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 78942615-[(4-Nitrophenoxy)methyl]-3-phenyl-1,2,4-oxadiazole

Product 1

HCID 220603435-[(4-Aminophenoxy)methyl]-3-phenyl-1,2,4-oxadiazoleYield 51.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The 5-[(4-nitrophenoxy)methyl]-3-phenyl-1,2,4-oxadiazole (0.5 g, 1.68 mmole) was dissolved in methanol:methylenechloride (1:1) (120 mL). Aqueous solution of (15 mL) sodium hydrosulfite (0.88 g, 5.05 mmole) and K2CO3 (0.70 g, 5.06 mmole) was added dropwise under nitrogen for 10 min. The contents were allowed to stir at room temperature. After consumption of starting material, reaction mixture was concentrated, diluted with water till the homogeneous layer formed. The aqueous layer was extracted with several times with ethylacetate and methylene chloride. The turbid organic layers were combined, dried with anhydrous Na2SO4 and concentrated. Purification of the solid concentrate by silica gel chromatography provided 5-[(4-aminophenoxy)methyl]-3-phenyl-1,2,4-oxadiazole (0.23 g, 51%). 1H NMR (CDCl3): δ 8.11 (m, 2H), 7.52-7.46 (m, 3H), 6.87 (d, 2H, J=8.8 Hz), 6.64 (d, 2H, J=8.8 Hz), 5.26 (s, 2H), 3.49 (br s, 2H).

Workup

  1. customAfter consumption of starting material, reaction mixture
  2. concentrationwas concentrated
  3. additiondiluted with water till the homogeneous layer
  4. customformed
  5. extractionThe aqueous layer was extracted with several times with ethylacetate and methylene chloride
  6. dry with materialdried with anhydrous Na2SO4
  7. concentrationconcentrated
  8. customPurification of the solid
  9. concentrationconcentrate by silica gel chromatography

Sources & evidence

ORD record
ord-318cccbf1f1548e1afeff3c0043ed034
Source dataset
uspto-grants-2015_04
Patent number
US09018204B1

Reaction notes

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