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Dimethylcarbamoyl Chloride → 1-[2-(4-Cyanophenoxy)ethyl]-1-(2-hydroxyethyl)-3,3-dimethylurea

HRID 899128
ノート
印刷プレビュー

反応式

HRID 899128 の反応式
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26]>ClCCl.O>[C:12]([C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][OH:1])[C:25]([N:24]([CH3:28])[CH3:23])=[O:26])=[CH:15][CH:14]=1)#[N:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 690686254-{2-[(2-Hydroxyethyl)amino]ethoxy}benzonitrile

生成物 1

HCID 690725741-[2-(4-Cyanophenoxy)ethyl]-1-(2-hydroxyethyl)-3,3-dimethylurea収率 89.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344
Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

4-{2-[(2-Hydroxyethyl)amino]ethoxy}benzonitrile (5 g, 0.0242 mol; see Preparation C, step (ii) above) was taken in dry dichloromethane (50 mL) and cooled to 0° C. Triethylamine (4 mL, 0.03 mol), followed by N,N-dimethylcarbamoyl chloride (3.9 g, 0.03 mol), was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. Purification by column chromatography using dichloromethane in methanol yielded 6 g of the sub-title compound as pale yellow liquid.

後処理

  1. additionwas added
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customPurification by column chromatography

出典と根拠

ORDレコード
ord-fa403931ca324fb4b549ad25703d6412
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07354917B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート