Cyanoacetamide → Dpn 205-734

HRID 371317Notes

Reaction equation

HRID 371317 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[Na].CN(C)[CH:10]=[C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[C:12](=O)[CH3:13]>C(O)C>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:11]2[CH:10]=[C:3]([C:1]#[N:2])[C:4](=[O:5])[NH:6][C:12]=2[CH3:13])=[CH:16][CH:17]=1)#[N:22]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 5360545Sodium2×HCID 542472714-[1-(Dimethylamino)-3-oxobut-1-en-2-yl]benzonitrile

Product 1

HCID 145915Dpn 205-734

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.2 g of cyanacetamide are added to a freshly prepared solution of 1.14 g sodium in 200 ml of absolute ethanol. 10.6 g 4-dimethylamino-3-(4-cyanophenyl)-3-buten-2-one are added and the solution is stirred 5 hours at boiling temperature, whereby the sodium salt of the title compound soon begins to crystallize out. The mixture is allowed to cool, the crystalline product is filtered and washed with ethanol and ether (m.p. of the sodium salt>300°) (m.p. of the free form>300°).

Sources & evidence

ORD record
ord-04f35d4ba1034a6c8a0255f24c217fb5
Source dataset
uspto-grants-1985_07
Patent number
US04530842

Reaction notes

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