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

HRID 349698

反応式

HRID 349698 の反応式
[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]

参加物

6

反応物 3

HCID 6916Diethylcarbamoyl chlorideHCID 11430Potassium CarbonateHCID 1413433-Morpholinophenol

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b76ca35572524a9080b7fb265fe43dee
出典データセット
uspto-grants-2007_02
特許番号
US07179912B2

関連ノート

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