Diethylcarbamoyl chloride → n,n-Diethyl-(3-morpholin-4-yl-phenoxy)carboxamide

HRID 884448

반응식

HRID 884448 반응식
[N:1]1([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:20]([N:22]([CH2:26][CH3:27])[C:23](Cl)=[O:24])[CH3:21]>C(#N)C.CCOC(C)=O>[CH2:20]([N:22]([CH2:26][CH3:27])[C:23]([O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[CH:8]=1)=[O:24])[CH3:21]

참가 물질

6

반응물 3

HCID 6916Diethylcarbamoyl chlorideHCID 11430Potassium CarbonateHCID 1413433-Morpholinophenol

생성물 1

HCID 9878759n,n-Diethyl-(3-morpholin-4-yl-phenoxy)carboxamide

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred mixture of 3-morpholinylphenol (0.34 g; 1.9 mmol) and powdered K2CO3 (0.576 g; 4.2 mmol) in dry acetonitrile (10 mL) was added diethyl carbamylchloride (0.26 mL; 2.0 mmol) via syringe at room temperature under nitrogen atmosphere. The resulting mixture was heated to reflux for 24 hours, then allowed to cool to room temperature. The reaction was diluted with EtOAc (60 mL), washed with water (2×20 mL) and brine, then dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified via radial chromatography (4 mm chromatotron plate with 2:1 hexanes/EtOAc) to provide the carbamate as a clear, colorless oil (0.39 g; 74%).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 24 hours
  3. washwashed with water (2×20 mL) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via radial chromatography (4 mm chromatotron plate with 2:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-bfd2928af0a441709b9d5e86ad7a596b
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242115B2

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