Methyl Isocyanate → HCID 20074956, compound

HRID 703824Notes

Reaction equation

HRID 703824 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH2:11][C:12]([O:14]C)=O)[NH2:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH3:16][N:17]=[C:18]=[O:19]>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:11][C:12](=[O:14])[N:17]([CH3:16])[C:18](=[O:19])[NH:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 54460083HCID 54460083, compound

Product 1

HCID 20074956HCID 20074956, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl [1-(3-cyanophenyl)hydrazino]acetate (700 mg) was dissolved in dry acetonitrile (10 ml) under nitrogen. Methyl isocyanate (0.7 ml) was added to the reaction mixture which was then heated at reflux for 1.5 h. The solvent was removed in vacuo and the oily residue was dissolved in methanol (10 ml) under nitrogen. Sodium methoxide (2.17M solution in methanol; 3.9 ml) was added and the solution was stirred at room temperature for 2 h. The reaction was poured into pH 6.5 phosphate buffer (100 ml) and extracted with ethyl acetate (3×80 ml). The combined, dried organic extracts were concentrated at reduced pressure to give a solid which was triturated with ether (3×20 ml) to give the title compound (640 mg), m.p. 174°-178°. N.m.r. indicated 0.084 mol ethyl acetate.

Workup

  1. temperaturewas then heated
  2. temperatureat reflux for 1.5 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe oily residue was dissolved in methanol (10 ml) under nitrogen
  5. additionSodium methoxide (2.17M solution in methanol; 3.9 ml) was added
  6. additionThe reaction was poured into pH 6.5 phosphate buffer (100 ml)
  7. extractionextracted with ethyl acetate (3×80 ml)
  8. concentrationdried organic extracts were concentrated at reduced pressure
  9. customto give a solid which
  10. customwas triturated with ether (3×20 ml)

Sources & evidence

ORD record
ord-b13d63bcd9134f4f83c834b5e33b3d1d
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

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