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

HRID 1981370ノート

反応式

HRID 1981370 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-101e15734b664f9b9f0e46e3a347d6e3
出典データセット
uspto-grants-1985_04
特許番号
US04514566

反応ノート

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