Water → 2-(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetamide

HRID 1698654Notes

Reaction equation

HRID 1698654 reaction equation
[NH4+]=[S:2].[CH3:3][O:4][C:5]1[C:14]2[O:13][CH2:12][O:11][CH2:10][C:9]=2[CH:8]=[C:7]([CH:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[N:29]=[C:28]([CH3:30])[O:27][N:26]=3)=[CH:21][CH:20]=2)[C:16]#[N:17])[CH:6]=1.C1COCC1.O>C(O)C.C(OCC)(=O)C>[CH3:3][O:4][C:5]1[C:14]2[O:13][CH2:12][O:11][CH2:10][C:9]=2[CH:8]=[C:7]([CH:15]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[N:29]=[C:28]([CH3:30])[O:27][N:26]=3)=[CH:23][CH:24]=2)[C:16]([NH2:17])=[S:2])[CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 59517220(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Product 1

HCID 595168152-(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 90 ml of a 20% aqueous solution of ammonium sulfide to a solution of 29.2 g of a crude (8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile in 240 ml of an ethanol:THF=2:1 mixed solvent, the mixture was stirred at room temperature for 8 hours. Water 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 the title compound (28.2 g, crude product) as a light yellow solid.

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-3767061cdd534eca90bc1e5760b8ecb3
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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