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

HRID 2079134Notes

Reaction equation

HRID 2079134 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-953e1ea67d1e47fab94416c95e6d1716
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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