Tetrahydrofuran → HCID 59517201, compound

HRID 1698616Notes

Reaction equation

HRID 1698616 reaction equation
[NH4+]=[S:2].[C:3]([CH:5]([NH:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[C:7]=1[F:16])#[N:4].C1COCC1.C(OCC)(=O)C>CO.O>[C:22]([C:21]1[CH:20]=[CH:19][C:18]([NH:17][CH:5]([C:6]2[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[C:7]=2[F:16])[C:3]([NH2:4])=[S:2])=[CH:25][CH:24]=1)#[N:23]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 59517247HCID 59517247, compound

Product 1

HCID 59517201HCID 59517201, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

After adding 14.2 ml of a 20% aqueous solution of ammonium sulfide to a solution of 2.59 g of 4-{[cyano-(2-fluoro-3,5-dimethoxyphenyl)methyl]amino}benzonitrile in 300 ml of a methanol:THF=2:1 mixed solvent, the mixture was stirred at room temperature for 16 hours. Then, a further 14.2 ml of a 20% aqueous solution of ammonium sulfide was added, and the mixture was stirred at room temperature for 24 hours. Next, 500 ml of ethyl acetate and 800 ml of water were added to the reaction mixture, and the organic layer was washed twice with 300 ml of water and then once with 300 ml of saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate (1:1)) to give the title compound (2.01 g) as a light yellow solid.

Workup

  1. washthe organic layer was washed twice with 300 ml of water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate (1:1))

Sources & evidence

ORD record
ord-f79538cec9404c02bffded43ac6fc4c3
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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