Ethyl Acetate → 2-(3,4-Dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetimidic acid methyl ester

HRID 2079178Notes

Reaction equation

HRID 2079178 reaction equation
F[B-](F)(F)F.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:16]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:31]=[C:30]([CH3:32])[O:29][N:28]=3)=[CH:23][CH:22]=2)[C:17]([NH2:19])=[S:18])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[C:33](OCC)(=O)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:33][S:18][C:17](=[NH:19])[CH:16]([C:10]1[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:8]([O:7][CH3:6])[CH:9]=1)[NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:31]=[C:30]([CH3:32])[O:29][N:28]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 26255TetrafluoroborateHCID 516892Sodium BicarbonateHCID 595168222-(3,4-Dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetamide

Product 1

HCID 595168142-(3,4-Dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetimidic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding 170 mg of Me3O+BF4− to a solution of 385 mg of 2-(3,4-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetamide in 30 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred at room temperature for 18 hours. Next, 200 ml of ethyl acetate and 100 ml of a 5% aqueous sodium hydrogen carbonate solution were added to the reaction mixture. The organic layer was washed 100 ml of saturated brine and dried over anhydrous magnesium sulfate. The desiccating agent was filtered, and the filtrate was concentrated under reduced pressure to give the title compound (371 mg, crude product).

Workup

  1. washThe organic layer was washed 100 ml of saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d5a96b540f0844cf934651636fc847a6
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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