Dimethylformamide → HCID 178473878, compound

HRID 2195694Notes

Reaction equation

HRID 2195694 reaction equation
C(#N)C([CH2:4][C:5]#[N:6])O.[H-].[Na+].[C:10]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:30]=[C:23]3[C:24]([O:26][C:27](=O)[NH:28][C:22]3=[CH:21][CH:20]=2)=O)[CH2:15][CH2:14]1)(=[O:12])[CH3:11].C[N:32](C)C=O>O>[NH2:32][C:27]1[C:4]([C:5]#[N:6])=[C:24]([OH:26])[C:23]2[C:22](=[CH:21][CH:20]=[C:19]([N:16]3[CH2:15][CH2:14][N:13]([C:10](=[O:12])[CH3:11])[CH2:18][CH2:17]3)[CH:30]=2)[N:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 212535622-HydroxybutanedinitrileHCID 866445955-(4-Acetylpiperazin-1-yl)isatoic anhydride

Product 1

HCID 178473878HCID 178473878, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 g malonitrile is dissolved in 50 ml dimethylformamide and in several portions 2.4 g sodium hydride 60% dispersion is added to it. To the clear solution 8 g 5-(4-acetylpiperazin-1-yl)isatoic anhydride is added and the mixture is stirred at room temperature for 10 hours. The reaction mixture is diluted with 70 ml water and extracted with 2×30 ml ethyl acetate. The aqueous phase is evaporated to dryness at reduced pressure, the solid residue is dissolved in 20 ml water and the pH is adjusted to 6 with acetic acid. The precipitated material is filtered off and washed with water. After drying 6.5 g of the title compound is obtained (MH+: 312).

Workup

  1. additionis added to it
  2. extractionextracted with 2×30 ml ethyl acetate
  3. customThe aqueous phase is evaporated to dryness at reduced pressure
  4. dissolutionthe solid residue is dissolved in 20 ml water
  5. filtrationThe precipitated material is filtered off
  6. washwashed with water
  7. dry with materialAfter drying 6.5 g of the title compound
  8. customis obtained (MH+: 312)

Sources & evidence

ORD record
ord-149eb52dbc834748862e406c6904ed90
Source dataset
uspto-grants-2012_12
Patent number
US08338411B2

Reaction notes

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