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Aniline → N-(1-ethoxy-2,2,2-trifluoroethyl)aniline

HRID 2193763
ノート
印刷プレビュー

反応式

HRID 2193763 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][CH:11](O)[C:12]([F:15])([F:14])[F:13])[CH3:9]>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:8]([O:10][CH:11]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]([F:15])([F:14])[F:13])[CH3:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 6115AnilineHCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-

生成物 1

HCID 12990236N-(1-ethoxy-2,2,2-trifluoroethyl)aniline収率 86.7%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 702Ethanol溶媒

実験手順

A solution of aniline (2 mL, 21.9 mmol), trifluoroacetaldehyde ethyl hemiacetal (2.6 mL, 21.9 mmol) and p-toluenesulfonic acid monohydrate (220 mg, 1.16 mmol) in ethanol (25 mL) was heated to reflux for 3 h under continuous stirring. The reaction mixture was cooled, the solvent was removed under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to afford title compound 325 (4.16 g, crude) as a yellow oil which was used directly for the next step.

後処理

  1. temperatureto reflux for 3 h under continuous stirring
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-c3023dd08b4a44a39e8234e5482dea78
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329726B2

反応ノート

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