Dimethylformamide → HCID 178510458, compound

HRID 655709Notes

Reaction equation

HRID 655709 reaction equation
C(#N)C([CH2:4][C:5]#[N:6])O.[H-].[Na+].[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:34]=[C:27]3[C:28](O[C:31](=O)[NH:32][C:26]3=[CH:25][CH:24]=2)=[O:29])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[N:36](C)C=O>O>[NH2:36][C:31]1[C:4]([C:5]#[N:6])=[C:28]([OH:29])[C:27]2[C:26](=[CH:25][CH:24]=[C:23]([N:20]3[CH2:21][CH2:22][N:17]([CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:18][CH2:19]3)[CH:34]=2)[N:32]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 212535622-HydroxybutanedinitrileHCID 86607778HCID 86607778, compound

Product 1

HCID 178510458HCID 178510458, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.1 g of malonitrile is dissolved in 100 mL of dimethylformamide. To the solution, in several portions, 3.6 g of 60% oily dispersion of sodium hydride are added. To the clear solution 18 g of 5-(4-benzylpiperazin-1-yl)isatoic anhydride is added and the mixture is stirred at room temperature for 10 hours. The reaction mixture is diluted with 100 mL of water and extracted with 2×50 mL of ethyl acetate. The aqueous phase is evaporated in vacuum, the solid residue is dissolved in 50 mL of water, the pH is adjusted to 6 with acetic acid and refluxed for 5 hours. After cooling the precipitated material is filtered off, washed with water. After drying 14.3 g of the title compound is obtained, m.p.: 291° C.

Workup

  1. extractionextracted with 2×50 mL of ethyl acetate
  2. customThe aqueous phase is evaporated in vacuum
  3. dissolutionthe solid residue is dissolved in 50 mL of water
  4. temperaturerefluxed for 5 hours
  5. temperatureAfter cooling the precipitated material
  6. filtrationis filtered off
  7. washwashed with water
  8. dry with materialAfter drying 14.3 g of the title compound
  9. customis obtained

Sources & evidence

ORD record
ord-cee1e8d127454c91b0de7d77ef5ae1ca
Source dataset
uspto-grants-2011_12
Patent number
US08071601B2

Reaction notes

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