Methyl Isocyanate → HCID 54023924, compound

HRID 1262811Notes

Reaction equation

HRID 1262811 reaction equation
[C:1]([CH2:4][S:5][C:6](=[N:13][OH:14])[C:7]([N+:10]([O-:12])=[O:11])([CH3:9])[CH3:8])(=[O:3])[NH2:2].[CH3:15][N:16]=[C:17]=[O:18]>C(N(CC)CC)C.C(#N)C>[CH3:15][NH:16][C:17]([O:14][N:13]=[C:6]([S:5][CH2:4][C:1](=[O:3])[NH2:2])[C:7]([N+:10]([O-:12])=[O:11])([CH3:9])[CH3:8])=[O:18]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 86739471HCID 86739471, compound

Product 1

HCID 54023924HCID 54023924, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 10 g (0.045 m) of 1-(carbamoylmethylthio)-2-nitro-2-methylpropionaldoxime, 150 ml. acetonitrile, 8.0 g (0.14 m) of methylisocyanate and three drops of triethylamine was allowed to stand at room temperature, with occasional shaking, for twenty hours. The acetonitrile and excess methyl isocyanate was removed from the product under reduced pressure. The solid residue was recrystallized from isopropanol and then dried at room temperature to give 9.0 g (72% yield) of 1-(carbamoylmethylthio)-2-nitro-2-methylpropionaldehyde O-(methylcarbamoyl)oxime; melting point=125-127° C. The nmr spectra confirmed the structure.

Workup

  1. waitto stand at room temperature, with occasional shaking, for twenty hours
  2. customThe acetonitrile and excess methyl isocyanate was removed from the product under reduced pressure
  3. customThe solid residue was recrystallized from isopropanol
  4. customdried at room temperature

Sources & evidence

ORD record
ord-2314a454d7ea467692dce4ab8c3456db
Source dataset
uspto-grants-1984_06
Patent number
US04454134

Reaction notes

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