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Water → 6-[3-(1,3-Dimethyl-3-cyclohexylureido)propoxy]carbostyril

HRID 1856767
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HRID 1856767 반응식
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2.[CH3:18][N:19]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:20](Cl)=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2)[C:20]([N:19]([CH3:18])[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:21]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 130557376-(3-Methylaminopropoxy)carbostyrilHCID 15209947N-cyclohexyl-N-methylcarbamoyl chloride

생성물 1

HCID 221326006-[3-(1,3-Dimethyl-3-cyclohexylureido)propoxy]carbostyril수율 47.9%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

6-(3-Methylaminopropoxy)carbostyril (3 g) is dissolved in dimethylformamide (150 ml), and thereto are added N-methyl-N-cyclohexylaminocarbonyl chloride (2.3 g) and potassium carbonate (2 g). The mixture is stirred at room temperature overnight, and further heated with stirring at 80° C. for 2 hours. The reaction solution is poured into water, and extracted with ethyl acetate. The extract is concentrated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=30:1), and recrystallized from ethyl acetate to give 6-[3-(1,3-dimethyl-3-cyclohexylureido)propoxy]carbostyril (2.3 g) as a white powder.

후처리

  1. temperaturefurther heated
  2. stirringwith stirring at 80° C. for 2 hours
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract is concentrated under reduced pressure
  5. customto remove the solvent
  6. customthe residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=30:1)
  7. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-538431f7e53e4cb299e9d71d87f0aff1
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06143763

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