Tetrahydrofuran → HCID 59517007, compound

HRID 1161363Notes

Reaction equation

HRID 1161363 reaction equation
[NH4+]=[S:2].[F:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]=[C:27]([CH3:29])[O:26][N:25]=2)=[CH:20][CH:19]=1)[C:15]#[N:16].O1CCCC1.C(OCC)(=O)C>CO.O>[F:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH:14]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[N:28]=[C:27]([CH3:29])[O:26][N:25]=2)=[CH:22][CH:23]=1)[C:15]([NH2:16])=[S:2]

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 59517354HCID 59517354, compound

Product 1

HCID 59517007HCID 59517007, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

After adding 36.8 ml of a 20% aqueous solution of ammonium sulfide to a solution of 7.97 g of (2-fluoro-4,5-dimethoxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile in 750 ml of a methanol:tetrahydrofuran (hereinafter, “THF”)=2:1 mixed solvent, the mixture was stirred at room temperature for 22 hours. Next, 1500 ml of ethyl acetate and 1000 ml of water were added to the reaction mixture, stirring was carried out at room temperature for 15 minutes, and the precipitate was filtered off. The organic layer in the filtrate was washed with saturated brine and dried over anhydrous sodium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure and combined with the previously obtained precipitate to give the title compound (8.59 g) as a light yellow solid.

Workup

  1. filtrationthe precipitate was filtered off
  2. washThe organic layer in the filtrate was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-028e324ed8f04929b0e9d89b93afc2db
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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