Dimethylformamide → HCID 178482613, compound

HRID 1985678Notes

Reaction equation

HRID 1985678 reaction equation
C(#N)C([CH2:4][C:5]#[N:6])O.[H-].[Na+].[CH3:10][N:11]([CH3:24])[C:12]1[CH:23]=[C:16]2[C:17]([O:19][C:20](=O)[NH:21][C:15]2=[CH:14][CH:13]=1)=O.C[N:26](C)C=O>O>[NH2:26][C:20]1[C:4]([C:5]#[N:6])=[C:17]([OH:19])[C:16]2[C:15](=[CH:14][CH:13]=[C:12]([N:11]([CH3:10])[CH3:24])[CH:23]=2)[N:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 127157955-Dimethylaminoisatoic anhydrideHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 178482613HCID 178482613, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of 4 g of malonitrile in 50 mL of dimethylformamide in several portions 2.4 g of sodium hydride 60% oily dispersion is added. To the clear solution 8 g of 5-dimethylamino-isatoic anhydride is added and the mixture is stirred at room temperature for 10 hours. The 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, and washed with water. After drying 6.5 g of the title compound is obtained, m.p.: 360° 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 6.5 g of the title compound
  7. customis obtained

Sources & evidence

ORD record
ord-3a75bff71d42403a95f97b7de690a1cc
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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