Methyl Isocyanate → HCID 20074957, compound

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:10][C:11]([O:13]C)=O)[NH2:9])=[CH:4][CH:3]=1.[CH3:15][N:16]=[C:17]=[O:18].C[O-].[Na+]>C(#N)C>[CH3:15][N:16]1[C:11](=[O:13])[CH2:10][N:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[NH:9][C:17]1=[O:18]

Participants

Procedure

To a solution of methyl [1-(4-methylphenyl)hydrazino]acetate (2.25 g) in acetonitrile (10 ml) was added methyl isocyanate (2 ml) and the mixture was heated under reflux for 30 min. The solvent was removed in vacuo to give a solid which was treated with a solution of sodium methoxide (27 ml; from sodium (4 g) and methanol (200 ml)) according to the method of Example 3 to give a solid which was purified by trituration with System A (1:1) to give the title compound (1.51 g), m.p. 193°-194°, t.l.c. (ether) Rf 0.56.