Potassium Carbonate → 5-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(di-n-butylaminosulphenyl)-N-methylcarbamoyl]oxime

HRID 2296037Notes

Reaction equation

HRID 2296037 reaction equation
[N:1](=[C:3]1[S:7][C:6]([CH3:9])([CH3:8])[N:5]=[C:4]1[CH3:10])[OH:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([N:21]([CH2:28][CH2:29][CH2:30][CH3:31])[S:22][N:23]([CH3:27])[C:24](F)=[O:25])[CH2:18][CH2:19][CH3:20]>C(#N)C>[CH2:17]([N:21]([CH2:28][CH2:29][CH2:30][CH3:31])[S:22][N:23]([CH3:27])[C:24]([O:2][N:1]=[C:3]1[S:7][C:6]([CH3:9])([CH3:8])[N:5]=[C:4]1[CH3:10])=[O:25])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12799219N-(di-n-butylaminosulfenyl)-N-fluorocarbonyl-N-methylamineHCID 1362290545-Oxo-2,2,4-trimethyl-3-thiazoline oxime

Product 1

HCID 545025405-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(di-n-butylaminosulphenyl)-N-methylcarbamoyl]oxime

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3.0 g (0.019 mol) of 5-oxo-2,2,4-trimethyl-3-thiazoline oxime are suspended in 10 ml of absolute acetonitrile. To the suspension at 0° C. there are successively added 5.5 g of anhydrous potassium carbonate and, dropwise, a solution of 4.52 g of N-(di-n-butylaminosulphenyl)-N-methylcarbamoyl fluoride in 10 ml of absolute acetonitrile. The reaction mixture is allowed to stir well at room temperature for 20 hours. Subsequently, the precipitated potassium salt is filtered off, and the filtrate is evaporated. Chromatography of the crude oily product on silica gel with ethyl acetate/toluene (1:3) as the eluent yields 5-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(di-n-butylaminosulphenyl)-N-methylcarbamoyl]oxime, nD20 1.5200.

Workup

  1. customat 0° C.
  2. filtrationSubsequently, the precipitated potassium salt is filtered off
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-860b4312510042f7ac1f1cf1209cdd7e
Source dataset
uspto-grants-1984_01
Patent number
US04427687

Reaction notes

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