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

HRID 1981372Notes

Reaction equation

HRID 1981372 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-bf1d9ff86c1045608c73b762138fb7ee
Source dataset
uspto-grants-1985_04
Patent number
US04514566

Reaction notes

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