Dimethylformamide → HCID 178480635, compound

HRID 1985670Notes

Reaction equation

HRID 1985670 reaction equation
C(#N)C([CH2:4][C:5]#[N:6])O.[H-].[Na+].[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:28]=[C:21]3[C:22]([O:24][C:25](=O)[NH:26][C:20]3=[CH:19][CH:18]=2)=O)[CH2:13][CH2:12]1.C[N:30](C)C=O>O>[NH2:30][C:25]1[C:4]([C:5]#[N:6])=[C:22]([OH:24])[C:21]2[C:20](=[CH:19][CH:18]=[C:17]([N:14]3[CH2:13][CH2:12][N:11]([CH3:10])[CH2:16][CH2:15]3)[CH:28]=2)[N:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 212535622-HydroxybutanedinitrileHCID 86607777HCID 86607777, compound

Product 1

HCID 178480635HCID 178480635, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g of malonitrile is dissolved in 30 mL of dimethylformamide. To the solution, in several portions, 1.3 g of 60% oily dispersion of sodium hydride are added. To the clear solution 6.5 g of 5-(4-methylpiperazino)isatoic acid anhydride is added and the mixture is stirred at room temperature for 10 hours. The reaction mixture is diluted with 70 mL of water and extracted with 2×30 mL of ethyl acetate. The aqueous phase is evaporated in vacuum, the solid residue is dissolved in 20 mL of water, the pH is adjusted to 6 with acetic acid. The precipitated material is filtered off, washed with water. After drying 5.2 g of the title compound is obtained, m.p.: 156° C.

Workup

  1. extractionextracted with 2×30 mL of ethyl acetate
  2. customThe aqueous phase is evaporated in vacuum
  3. dissolutionthe solid residue is dissolved in 20 mL of water
  4. filtrationThe precipitated material is filtered off
  5. washwashed with water
  6. dry with materialAfter drying 5.2 g of the title compound
  7. customis obtained

Sources & evidence

ORD record
ord-1e390a1e74f14b89944016fe569c608f
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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