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Dimethylcarbamoyl Chloride → 1-[3-(4-Cyanophenyl)propyl]-1-(2-hydroxyethyl)-3,3-dimethylurea

HRID 899134
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HRID 899134 반응식
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[OH:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl.O>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([CH2:13][CH2:12][CH2:11][N:10]([CH2:9][CH2:8][OH:7])[C:3]([N:2]([CH3:6])[CH3:1])=[O:4])=[CH:15][CH:16]=1)#[N:19]
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참가 물질

6

반응물 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 690715794-[3-(2-Hydroxyethylamino)propyl]benzonitrile

생성물 1

HCID 690676201-[3-(4-Cyanophenyl)propyl]-1-(2-hydroxyethyl)-3,3-dimethylurea수율 101.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6344
Dichloromethane
용매

실험 절차

N,N-Dimethylcarbamoyl chloride (3.9 g, 0.0368 mol) was added to a mixture of 4-[3-(2-hydroxyethylamino)propyl]benzonitrile (5 g, 0.025 mol; see step (i) above) and triethylamine (3.7 g, 0.368 mol) in dichloromethane (100 mL) at 0° C. Stirring was then continued 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. Solvent evaporation under reduced pressure, followed by purification by column chromatography (using 4% methanol in dichloromethane) yielded 7 g of the sub-title compound as a pale yellow, gummy liquid.

후처리

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customSolvent evaporation under reduced pressure
  5. customfollowed by purification by column chromatography (using 4% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-4740ed437ffa44a6be61577d8a64ec8e
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07354917B2

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