Tetrahydrofuran → 4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-N2-(4-methoxyphenyl)benzene-1,2-diamine

HRID 452611Notes

Reaction equation

HRID 452611 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[F:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][C:18]2[O:22][C:21]([C:23]3[CH:24]=[CH:25][C:26]([N+:38]([O-])=O)=[C:27]([CH:37]=3)[NH:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[N:20][N:19]=2)[CH:13]=[CH:14][CH:15]=1.O1CCCC1.C(=O)([O-])O.[Na+]>C(O)C>[F:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][C:18]2[O:22][C:21]([C:23]3[CH:37]=[C:27]([NH:28][C:29]4[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=4)[C:26]([NH2:38])=[CH:25][CH:24]=3)=[N:20][N:19]=2)[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 686638085-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-N-(4-methoxyphenyl)-2-nitroaniline

Product 1

HCID 686641364-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-N2-(4-methoxyphenyl)benzene-1,2-diamineYield 72.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an aqueous solution (5.1 mL) of sodium hydrosulfite (1.15 g, 6.61 mmol) was added a mixed solution of 5-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-N-(4-methoxyphenyl)-2-nitroaniline (0.20 g, 0.41 mmol), tetrahydrofuran (4.1 mL) and ethanol (2.1 mL) at 0° C., and the resulting mixture was stirred at room temperature for 30 min. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound (0.12 g, yield 71%) as a 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 anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-43654c58f3c64b138fce4cb5ba24cee4
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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