Methyl Isocyanate → HCID 20074957, compound

HRID 703819Notes

Reaction equation

HRID 703819 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

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 10942334Sodium MethoxideHCID 53894127HCID 53894127, compound

Product 1

HCID 20074957HCID 20074957, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. customThe solvent was removed in vacuo
  4. customto give a solid which
  5. customto give a solid which
  6. customwas purified by trituration with System A (1:1)

Sources & evidence

ORD record
ord-8c5afcbe0a3c4fdebb882f9eaaa8a467
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

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