Water → 2-(4-Methoxy-3-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetamide

HRID 1161389Notes

Reaction equation

HRID 1161389 reaction equation
[NH4+]=[S:2].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]=[C:24]([CH3:26])[O:23][N:22]=3)=[CH:17][CH:16]=2)[C:12]#[N:13])=[CH:7][C:6]=1[O:27][Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30].C1COCC1.O>CO.C(OCC)(=O)C>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:25]=[C:24]([CH3:26])[O:23][N:22]=3)=[CH:19][CH:20]=2)[C:12]([NH2:13])=[S:2])=[CH:7][C:6]=1[O:27][Si:28]([CH:29]([CH3:30])[CH3:31])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 59516995(4-Methoxy-3-triisopropylsilanyloxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Product 1

HCID 595170242-(4-Methoxy-3-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 30.8 ml of a 20% aqueous solution of ammonium sulfide to a solution of 8.92 g of (4-methoxy-3-triisopropylsilanyloxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile in 300 ml of a methanol:THF=2:1 mixed solvent, the mixture was stirred at room temperature for 15 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. After washing the organic layer with saturated brine, it was dried over anhydrous sodium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (8.59 g) as a crude product.

Workup

  1. washAfter washing the organic layer with saturated brine, it
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-04e512fe53e540a6b331dc4a1ea4afb5
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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