Triethylamine → 3,3-Dimethyl-4-fluoro-1-methylthio-2-hydroximino-butane

HRID 1447432Notes

Reaction equation

HRID 1447432 reaction equation
[CH3:1][C:2]([CH3:10])([CH2:8][F:9])[C:3](=O)[CH2:4][S:5][CH3:6].Cl.[NH2:12][OH:13].C(N(CC)CC)C>C(O)C>[CH3:1][C:2]([CH3:10])([CH2:8][F:9])[C:3](=[N:12][OH:13])[CH2:4][S:5][CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 128972673,3-Dimethyl-4-fluoro-1-methylthio-butan-2-one

Product 1

HCID 887514843,3-Dimethyl-4-fluoro-1-methylthio-2-hydroximino-butaneYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

99 g (0.6 mol) of 3,3-dimethyl-4-fluoro-1-methylthiobutan -2-one, 46 g (0.66 mol) of hydroxylamine hydrochloride and 66.7 g (0.66 mol) of triethylamine in 300 ml of ethanol were heated under reflux for 6 hours. The solvent was then removed in vacuo, the residue was partitioned between methylene chloride and water and the methylene chloride phase was separated off and dried with sodium sulphate. After distilling off the solvent, the residue was distilled in vacuo. 80 g (75% of theory) of 3,3-dimethyl-4-fluoro-1-methylthio-2-hydroximino-butane of boiling point 133° C./13 mm Hg were obtained. ##STR31## 78 g (0.43 mol) of 3,3-dimethyl-4-fluoro-1-methylthio-hydroximinobutane were dissolved in 300 ml of methylene chloride, and 26 g (0.46 mol) of methyl isocyanate were added dropwise. During this addition, the temperature of the reaction solution rose to about 35° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe solvent was then removed in vacuo
  3. customthe residue was partitioned between methylene chloride and water
  4. customthe methylene chloride phase was separated off
  5. dry with materialdried with sodium sulphate
  6. distillationAfter distilling off the solvent
  7. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-7152c01e25bd4f9fa6760e91a9e92f85
Source dataset
uspto-grants-1982_02
Patent number
US04316910

Reaction notes

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