Methyl Isocyanate → Ethanimidothioic acid, 2,2,2-trifluoro-N-[[(methylamino)carbonyl]oxy]-, methyl ester, (E)-

HRID 1074908Notes

Reaction equation

HRID 1074908 reaction equation
[F:1][C:2]([F:9])([F:8])/[C:3](=[N:6]\[OH:7])/[S:4][CH3:5].[CH3:10][N:11]=[C:12]=[O:13]>C(N(CC)CC)C>[F:1][C:2]([F:9])([F:8])/[C:3](=[N:6]\[O:7][C:12](=[O:13])[NH:11][CH3:10])/[S:4][CH3:5]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 13003317HCID 13003317, compound

Product 1

HCID 9577256Ethanimidothioic acid, 2,2,2-trifluoro-N-[[(methylamino)carbonyl]oxy]-, methyl ester, (E)-Yield 74%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

One drop of triethylamine was added to a mixture of 6.37 g (0.04 mol) of S-methyl (E)-2,2,2-trifluoro-N-hydroxythioacetimidate and 2.28 g (0.04 mol) of methyl isocyanate. An exothermic reaction ensued, and the reaction mixture was cooled in an ice-bath. The reaction mixture solidified on cooling. Recrystallization from ether gave 6.39 g (74% yield) of S-methyl (E)-2,2,2-trifluoro-N-(methylcarbamoyloxy)thioacetimidate as colorless crystals., mp. 83°-85°. Analysis of the isomer prepared in a similar procedure follows:

Workup

  1. customAn exothermic reaction
  2. temperaturethe reaction mixture was cooled in an ice-bath
  3. temperatureon cooling
  4. customRecrystallization from ether

Sources & evidence

ORD record
ord-66b74a83b0544dac9fa58a4ed3ed6326
Source dataset
uspto-grants-1983_07
Patent number
US04394386

Reaction notes

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