Potassium Hydroxide → 1-methylthio-3,3-dimethyl-2-butanone O-[N-methyl-N-(dimethylaminosulfenyl)carbamoyl]oxime

HRID 1447120Notes

Reaction equation

HRID 1447120 reaction equation
[OH-].[K+].C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3.[CH3:29][S:30][CH2:31][C:32](=[N:37][OH:38])[C:33]([CH3:36])([CH3:35])[CH3:34].[CH3:39][N:40]([S:44][N:45]([CH3:47])[CH3:46])[C:41](F)=[O:42]>C1C=CC=CC=1>[CH3:39][N:40]([S:44][N:45]([CH3:47])[CH3:46])[C:41]([O:38][N:37]=[C:32]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:31][S:30][CH3:29])=[O:42]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 382321-Methylthio-3,3-dimethyl-2-butanone oximeHCID 85955Dicyclohexano-18-crown-6HCID 12799216N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluoride

Product 1

HCID 544754281-methylthio-3,3-dimethyl-2-butanone O-[N-methyl-N-(dimethylaminosulfenyl)carbamoyl]oximeYield 73.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.5 g powdered potassium hydroxide, 0.1 g. of dicyclohexyl-18-crown-6, and 6.0 g (0.037 mole) of 1-methylthio-3,3-dimethyl-2-butanone oxime in 200 ml of benzene was stirred 2 hrs. at 28° C. Then 5.9 g (0.037 mole) of N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluoride was added rapidly. The mixture was stirred 20 hrs. at room temperature, water washed three times, dried (MgSO4), and the benzene solvent was removed in vacuo. The product, 1-methylthio-3,3-dimethyl-2-butanone O-[N-methyl-N-(dimethylaminosulfenyl)carbamoyl]oxime, was obtained as a heavy syrup which would not crystallize, 8 g. (73.7 percent yield).

Workup

  1. additionA mixture of 2.5 g
  2. customat 28° C
  3. washat room temperature, water washed three times
  4. dry with materialdried (MgSO4)
  5. customthe benzene solvent was removed in vacuo

Sources & evidence

ORD record
ord-44622b2b1de14e7ea9f5239c006d36a6
Source dataset
uspto-grants-1982_02
Patent number
US04315928

Reaction notes

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