Methyl Isocyanate → HCID 53713561, compound

HRID 1262810Notes

Reaction equation

HRID 1262810 reaction equation
[C:1]([CH2:4][CH:5]([CH3:11])[S:6][C:7](=[N:9][OH:10])[CH3:8])(=[O:3])[NH2:2].[CH3:12][N:13]=[C:14]=[O:15]>C(N(CC)CC)C.CC(C)=O>[CH3:12][NH:13][C:14]([O:10][N:9]=[C:7]([S:6][CH:5]([CH3:11])[CH2:4][C:1](=[O:3])[NH2:2])[CH3:8])=[O:15]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 86254502HCID 86254502, compound

Product 1

HCID 53713561HCID 53713561, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 3.0 g (0.017 m) of 1-(2-carbamoyl-1-methylethylthio)acetaldoxime, 200 ml. of dry acetone, 3.0 g. (0.053 m) of methyl isocyanate, and two drops of triethylamine was allowed to stand at room temperature, with occasional shaking, for two days. The acetone and excess methyl isocyanate was removed from the product under reduced pressure. The white solid residue was recrystallized from isopropanol and dried at room temperature to give 3.0 g (75% yield) of 1-(2-carbamoyl-1-methylethylthio)acetaldehyde O-(methylcarbamoyl)oxime; melting point=119-121. The nmr spectra confirmed the structure.

Workup

  1. customThe acetone and excess methyl isocyanate was removed from the product under reduced pressure
  2. customThe white solid residue was recrystallized from isopropanol
  3. customdried at room temperature

Sources & evidence

ORD record
ord-1cbd3f19f2bf4d158b317ad7e44527f7
Source dataset
uspto-grants-1984_06
Patent number
US04454134

Reaction notes

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