Methyl Isocyanate → 2-oxo-4,5,5-trimethyl-3-thiazoline-O-(methylcarbamoyl)-oxime

HRID 127211Notes

Reaction equation

HRID 127211 reaction equation
[N:1](=[C:3]1[N:7]=[C:6]([CH3:8])[C:5]([CH3:10])([CH3:9])[S:4]1)[OH:2].[CH3:11][N:12]=[C:13]=[O:14]>C(N(CC)CC)C.ClCCl>[CH3:11][NH:12][C:13]([O:2][N:1]=[C:3]1[N:7]=[C:6]([CH3:8])[C:5]([CH3:10])([CH3:9])[S:4]1)=[O:14]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 859972442-Oxo-4,5,5-trimethyl-3-thiazoline oxime

Product 1

HCID 867375512-oxo-4,5,5-trimethyl-3-thiazoline-O-(methylcarbamoyl)-oxime

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

15.8 g (0.1 mol) of 2-oxo-4,5,5-trimethyl-3-thiazoline-oxime and 8.5 g. (0.15 mol) of methyl isocyanate were dissolved in 100 ml. of anhydrous dichloromethane. After a few drops of triethylamine were added to this solution, the mixture warmed to 40°-45° C. The mixture was warmed to 50°-60° C. for a short time and then the solvent was distilled off under vacuum. The residue was dissolved in 50 ml. of hot ethyl acetate, treated with carbon and filtered. The hot filtrate was concentrated to 20-30 ml. and treated with 20-30 ml. of hexane. The precipitated crystals were filtered off under vacuum, washed with ether and dried to yield 2-oxo-4,5,5-trimethyl-3-thiazoline-O-(methylcarbamoyl)-oxime, m.p. 123°-125° C.

Workup

  1. temperaturethe mixture warmed to 40°-45° C
  2. temperatureThe mixture was warmed to 50°-60° C. for a short time
  3. distillationthe solvent was distilled off under vacuum
  4. dissolutionThe residue was dissolved in 50 ml
  5. additionof hot ethyl acetate, treated with carbon
  6. filtrationfiltered
  7. concentrationThe hot filtrate was concentrated to 20-30 ml
  8. additionand treated with 20-30 ml
  9. filtrationThe precipitated crystals were filtered off under vacuum
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-9d6fd169d45f4e3eab23bc59a7840168
Source dataset
uspto-grants-1981_03
Patent number
US04255436

Reaction notes

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