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Dimethylformamide → Hydratropamide, alpha-methyl-

HRID 2299090
ノート
印刷プレビュー

反応式

HRID 2299090 の反応式
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3](O)=[O:4].C[N:14](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3]([NH2:14])=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 132222-Phenylisobutyric acidHCID 65578Oxalyl chloride

生成物 1

HCID 94713Hydratropamide, alpha-methyl-収率 88%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

To a solution of 2-methyl-2-phenylpropionic acid in 100 mL of CH2Cl2 was added 0.50 mL of DMF and oxalyl chloride (3.40 g, 26.8 mmol). The mixture was stirred at 23° C. for 4 hours then the solvent was removed under reduced pressure. The crude material was dissolved in 50 mL of THF and 30 mL of NH4OH was added. The mixture was stirred at 23° C. for 1 hour then and the mixture was concentrated under reduced pressure. The crude product was dissolved in 150 mL of EtOAc and washed with 100 mL of 2 N HCl, 100 mL NaHCO3, and 100 mL of brine. The organic phase was dried over Na2SO4 and concentrated. The product was purified by recrystallization from EtOAc/hexanes to provide 3.50 g (88% yield) of the desired product as a white powder.

後処理

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe crude material was dissolved in 50 mL of THF
  3. addition30 mL of NH4OH was added
  4. stirringThe mixture was stirred at 23° C. for 1 hour
  5. concentrationthe mixture was concentrated under reduced pressure
  6. dissolutionThe crude product was dissolved in 150 mL of EtOAc
  7. washwashed with 100 mL of 2 N HCl, 100 mL NaHCO3, and 100 mL of brine
  8. dry with materialThe organic phase was dried over Na2SO4
  9. concentrationconcentrated
  10. customThe product was purified by recrystallization from EtOAc/hexanes

出典と根拠

ORDレコード
ord-e252db8fb7e14dabbd4c0db62e75b4eb
出典データセット
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06495576B2

反応ノート

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