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Dimethyl Sulfoxide → HCID 22493624、化合物

HRID 1263458
ノート
印刷プレビュー

反応式

HRID 1263458 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]1[C:13]([CH2:26][OH:27])=[N:14][C:15]2[C:16]([CH3:25])([CH3:24])[CH2:17][CH2:18][C:19]([CH3:23])([CH3:22])[C:20]=2[N:21]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.CCCCCC.O>[CH3:11][C:12]1[C:13]([CH:26]=[O:27])=[N:14][C:15]2[C:16]([CH3:25])([CH3:24])[CH2:17][CH2:18][C:19]([CH3:23])([CH3:22])[C:20]=2[N:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22493589HCID 22493589、化合物

生成物 1

HCID 22493624HCID 22493624、化合物収率 94.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒
3 回
HCID 21226206Ethyl acetate hexane溶媒

実験手順

A solution of 923 μl of dimethylsulfoxide in 2 ml of dichloromethane was added dropwise to a solution of 797 μl of oxalyl chloride in 6 ml of dichloromethane at −60° C. under a nitrogen gas stream, followed by stirring for 5 minutes. To the reaction mixture, a solution of 1 g of 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylquinoxaline-2-methanol in 6 ml of dichloromethane was added dropwise and the resulting mixture was stirred for 15 minutes. Triethylamine (4.8 ml) was then added dropwise to the reaction mixture, followed by stirring for 5 minutes. After the reaction mixture was raised to room temperature and stirred for 15 minutes, water was added thereto. The resulting mixture was extracted with dichloromethane. The organic layer was successively washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 10% ethyl acetate/n-hexane), whereby 940 mg of the title compound were obtained in the form of a pale yellow solid.

後処理

  1. stirringthe resulting mixture was stirred for 15 minutes
  2. stirringby stirring for 5 minutes
  3. stirringstirred for 15 minutes
  4. extractionThe resulting mixture was extracted with dichloromethane
  5. washThe organic layer was successively washed with water and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue so obtained

出典と根拠

ORDレコード
ord-543c21e175574f4eae906e8112d1af81
出典データセット
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06541474B2

反応ノート

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