Ethyl Acetate → HCID 67096803, compound

HRID 2079130Notes

Reaction equation

HRID 2079130 reaction equation
F[B-](F)(F)F.[CH3:6][O:7][C:8]1[C:13]2[O:14][CH2:15][CH2:16][O:17][C:12]=2[CH:11]=[C:10]([CH:18]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[N:33]=[C:32]([CH3:34])[O:31][N:30]=3)=[CH:25][CH:24]=2)[C:19]([NH2:21])=[S:20])[CH:9]=1.[C:35](=O)([O-])O.[Na+].C(OCC)(=O)C>C(#N)C>[CH3:35][S:20][C:19](=[NH:21])[CH:18]([C:10]1[CH:9]=[C:8]([O:7][CH3:6])[C:13]2[O:14][CH2:15][CH2:16][O:17][C:12]=2[CH:11]=1)[NH:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[N:33]=[C:32]([CH3:34])[O:31][N:30]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 26255TetrafluoroborateHCID 516892Sodium BicarbonateHCID 59517444HCID 59517444, compound

Product 1

HCID 67096803HCID 67096803, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After adding 750 mg of Me3O+BF4− to a solution of 1.92 g of 2-(8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetamide in 20 ml of acetonitrile, the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give 2-(8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetimidic acid methyl ester.

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationThe desiccating agent was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e116d42abe6c4ebda449fb0c9cec8f42
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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