Potassium Carbonate → HCID 22060343, compound

HRID 71340Notes

Reaction equation

HRID 71340 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 22060343HCID 22060343, compoundYield 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-e09d2758d1a140e995d3f3aa7526334b
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Reaction notes

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