Potassium Hydroxide → 2-methyl-2-(methylthio)propionaldehyde O-[N-methyl-N-(dimethylaminosulfenyl)carbamoyl]oxime

HRID 1447119Notes

Reaction equation

HRID 1447119 reaction equation
[OH-].[K+].[CH3:3][C:4]([S:9][CH3:10])([CH3:8])[CH:5]=[N:6][OH:7].[CH3:11][N:12]([S:16][N:17]([CH3:19])[CH3:18])[C:13](F)=[O:14]>C1C=CC=CC=1.C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3>[CH3:11][N:12]([S:16][N:17]([CH3:19])[CH3:18])[C:13]([O:7][N:6]=[CH:5][C:4]([CH3:8])([S:9][CH3:10])[CH3:3])=[O:14]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 154362-Methylthio-2-methylpropionaldoximeHCID 12799216N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluoride

Product 1

HCID 540037182-methyl-2-(methylthio)propionaldehyde O-[N-methyl-N-(dimethylaminosulfenyl)carbamoyl]oximeYield 75.5%

Reagents, catalysts & solvents 2

HCID 85955Dicyclohexano-18-crown-6CatalystHCID 241BenzeneSolvent

Procedure

A mixture of 3.3 g powdered potassium hydroxide, 0.1 g dicyclohexyl-18-crown-6, and 6.7 g (0.05 mole) of 2-methyl-2-(methylthio)propionaldehyde oxime in 200 ml of benzene was stirred 1 hr. at room temperature. N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluoride (8.0 g, 0.05 mole) was then added, and the mixture was stirred overnight at room temperature. The solution was extracted three times with water, dried (MgSO4), and concentrated in vacuo. The oily residue was recrystallized from n-hexane to give 10 g (75.5 percent yield) of 2-methyl-2-(methylthio)propionaldehyde O-[N-methyl-N-(dimethylaminosulfenyl)carbamoyl]oxime, m.p. 48°-50° C.

Workup

  1. additionA mixture of 3.3 g
  2. customat room temperature
  3. stirringthe mixture was stirred overnight at room temperature
  4. extractionThe solution was extracted three times with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-46465e08f54040c38ed3626c295c8688
Source dataset
uspto-grants-1982_02
Patent number
US04315928

Reaction notes

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