Dimethylcarbamoyl Chloride → 5-oxo-2,2,4-trimethyl-3-thiazoline O-(dimethylcarbamoyl)oxime

HRID 2296035노트

반응식

HRID 2296035 반응식
[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]

참가 물질

6

반응물 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 1362290545-Oxo-2,2,4-trimethyl-3-thiazoline oxime

생성물 1

HCID 544526015-oxo-2,2,4-trimethyl-3-thiazoline O-(dimethylcarbamoyl)oxime

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. 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
  2. stirringthe reaction mixture is stirred at room temperature for 16 hours
  3. washthe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent is subsequently distilled off
  6. customthe residue is recrystallized from diethyl ether/n-hexane

출처 및 근거

ORD 기록
ord-927634a3cf7a41979a5b3bcd29fc839b
출처 데이터셋
uspto-grants-1984_01
특허 번호
US04427687

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