Methyl Isocyanate → HCID 20074981, compound

HRID 703814Notes

Reaction equation

HRID 703814 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:10][C:11]([O:13]C)=O)[NH2:9])[CH:5]=[CH:6][CH:7]=1.[CH3:15][N:16]=[C:17]=[O:18]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:10][C:11](=[O:13])[N:16]([CH3:15])[C:17](=[O:18])[NH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 54396632HCID 54396632, compound

Product 1

HCID 20074981HCID 20074981, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl [1-(3-bromophenyl)hydrazino]acetate (2.5 g) and methyl isocyanate (1.46 ml) in acetonitrile (20 ml) was heated under reflux for 2 h. The solvent was removed in vacuo and methanol (20 ml) was added to the residue which was then treated with a solution of sodium methoxide in methanol (30 ml; from 556 mg of sodium). After 1 h at 20° the solution was neutralised with acetic and the solvent was removed in vacuo. The residue was taken into ethyl acetate (250 ml), washed with pH 6 phosphate buffer solution (250 ml), dried and evaporated. Crystallisation of the residue from System B gave the title compound (316 mg). The mother liquor was evaporated, and the resulting solid was triturated with ether to give a further quantity of the title compound (335 mg), m.p. 165°-166°, t.l.c. (ether) Rf 0.41.

Workup

  1. temperatureunder reflux for 2 h
  2. customThe solvent was removed in vacuo and methanol (20 ml)
  3. additionwas added to the residue which
  4. additionwas then treated with a solution of sodium methoxide in methanol (30 ml; from 556 mg of sodium)
  5. customthe solvent was removed in vacuo
  6. washwashed with pH 6 phosphate buffer solution (250 ml)
  7. customdried
  8. customevaporated
  9. customCrystallisation of the residue from System B

Sources & evidence

ORD record
ord-36875cb79aea4a85bbad704d1a18baa1
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

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