Methyl Isocyanate → HCID 20074964, compound

HRID 703820Notes

Reaction equation

HRID 703820 reaction equation
[F: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(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:10][C:11](=[O:13])[N:16]([CH3:15])[C:17](=[O:18])[NH:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 54168443HCID 54168443, compound

Product 1

HCID 20074964HCID 20074964, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl [1-(4-fluorophenyl)hydrazino]acetate (2.12 g) and methyl isocyanate (1.63 ml) in acetonitrile (20 ml) was heated under reflux for 3 h. The solvent was removed in vacuo and the residual oil was taken into methanol (20 ml) and treated with a solution of sodium methoxide (from sodium (556 mg) in methanol (30 ml)). After 1 h at 20° the solution was neutralised with acetic acid and the solvent was removed in vacuo. The residue was taken into ethyl acetate (100 ml), washed with pH 6 phosphate buffer (100 ml), dried and evaporated. Crystallisation of the residue from System B gave the title compound (1.10 g), m.p. 205°-206°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customThe solvent was removed in vacuo
  4. additiontreated with a solution of sodium methoxide (from sodium (556 mg) in methanol (30 ml))
  5. customthe solvent was removed in vacuo
  6. washwashed with pH 6 phosphate buffer (100 ml)
  7. customdried
  8. customevaporated
  9. customCrystallisation of the residue from System B

Sources & evidence

ORD record
ord-593a13a139a24c30bea8e20d5578f577
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

Loading…