Methyl Isocyanate → 2-Amino-1-methyl-2-oxoethyl N-(((methylamino)carbonyl)oxy)ethanimidothioate

HRID 1262809Notes

Reaction equation

HRID 1262809 reaction equation
[C:1]([CH:4]([S:6][C:7](=[N:9][OH:10])[CH3:8])[CH3:5])(=[O:3])[NH2:2].[CH3:11][N:12]=[C:13]=[O:14]>C(N(CC)CC)C.CC(C)=O>[CH3:11][NH:12][C:13]([O:10][N:9]=[C:7]([S:6][CH:4]([C:1](=[O:3])[NH2:2])[CH3:5])[CH3:8])=[O:14]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 86254504HCID 86254504, compound

Product 1

HCID 569894332-Amino-1-methyl-2-oxoethyl N-(((methylamino)carbonyl)oxy)ethanimidothioateYield 74%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 4.0 g (0.0247 m) of 1-(1-carbamoylethylthio)acetaldoxime, 75 ml of dry acetone, 4.0 g (0.07 m) of methyl isocyanate, and 2 drops of triethylamine was allowed to stand at room temperature, with occasional shaking, for two days. The acetone and excess methyl isocyanate were removed from the product under reduced pressure. The white solid residue was recrystallized from ethanol and then dried at room temperature to give 4.0 g (74% yield) of 1-(1-carbamoylethylthio]acetaldehyde O-(methylcarbamoyl)oxime; melting point=161°-163° C.

Workup

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

Sources & evidence

ORD record
ord-08d38cb326764b73a7d10ee925831b0f
Source dataset
uspto-grants-1984_06
Patent number
US04454134

Reaction notes

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