Cyanoacetic acid → HCID 15136415, compound

HRID 2050796Notes

Reaction equation

HRID 2050796 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.BrCC1C(C#N)=CC=CC=1.[CH3:21][N:22]=[C:23]=[O:24].[C:25]([CH2:27][C:28]([OH:30])=O)#[N:26]>>[NH2:26][C:25]1[N:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([C:2]#[N:1])=[CH:4][CH:5]=2)[C:23](=[O:24])[N:22]([CH3:21])[C:28](=[O:30])[CH:27]=1

Participants

5

Reactant 4

HCID 9740Cyanoacetic acidHCID 12228Methyl IsocyanateHCID 826084-(Aminomethyl)benzonitrileHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 15136415HCID 15136415, compound

Procedure

α-Amino-p-tolunitrile (prepared from α-bromotolunitrile in a modification of the method described by J. H. Short and T. D. Darby, J. Med. Chem., 10 (5), 833, 1967) was treated first with methyl isocyanate followed by cyanoacetic acid according to the method of V. Papesch and E. F. Schroeder (J. Org. Chem., 1951, 16, 1879) to yield 4-[(6-amino-1,2,3,4-tetrahydro-3-methyl-2,4-dioxo-1-pyrimidinyl)methyl]benzonitrile, which was then nitrosated, reduced, and condensed with 4-formylcinnamic acid following an analogous procedure to that of Example 3 to give the title compound as a yellow solid with a melting point greater than 350° C.

Sources & evidence

ORD record
ord-b4a08d975719406b8ff820ae42c47f8d
Source dataset
uspto-grants-1991_05
Patent number
US05015647

Reaction notes

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