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

HRID 899128
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HRID 899128 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fa403931ca324fb4b549ad25703d6412
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07354917B2

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