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

HRID 1161448Notes

Reaction equation

HRID 1161448 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-6f87cd32e0bf4636bf6b4153e4b77cc6
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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