Dimethylcarbamoyl Chloride → 5-oxo-2,2,4-trimethyl-3-thiazoline O-(dimethylcarbamoyl)oxime
Reaction equation
[N:1](=[C:3]1[S:7][C:6]([CH3:9])([CH3:8])[N:5]=[C:4]1[CH3:10])[OH:2].[H-].[Na+].[CH3:13][N:14]([CH3:18])[C:15](Cl)=[O:16]>O1CCCC1.C(OCC)C>[CH3:13][N:14]([CH3:18])[C:15]([O:2][N:1]=[C:3]1[S:7][C:6]([CH3:9])([CH3:8])[N:5]=[C:4]1[CH3:10])=[O:16]Participants
Procedure
3.0 g (0.019 mol) of 5-oxo-2,2,4-trimethyl-3-thiazoline oxime are added portionwise to a suspension of 0.9 g of sodium hydride in 20 ml of tetrahydrofuran. The sodium hydride was liberated shortly before its use from a 55% suspension in oil by two-fold extraction with a small amount of absolute pentane. After completion of the hydrogen evolution, the mixture is stirred at room temperature for an additional 1 hour. 2.05 g (0.019 mol) of dimethylcarbamoyl chloride are added dropwise, and the reaction mixture is stirred at room temperature for 16 hours. The residue is then taken up in diethyl ether, and the organic phase is washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is subsequently distilled off, and the residue is recrystallized from diethyl ether/n-hexane to yield 5-oxo-2,2,4-trimethyl-3-thiazoline O-(dimethylcarbamoyl)oxime, m.p. 92°-95° C.
Workup
- extractionThe sodium hydride was liberated shortly before its use from a 55% suspension in oil by two-fold extraction with a small amount of absolute pentane
- stirringthe reaction mixture is stirred at room temperature for 16 hours
- washthe organic phase is washed with saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent is subsequently distilled off
- customthe residue is recrystallized from diethyl ether/n-hexane
Sources & evidence
- ORD record
- ord-101e15734b664f9b9f0e46e3a347d6e3
- Source dataset
- uspto-grants-1985_04
- Patent number
- US04514566
Reaction notes
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