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Hydrochloric Acid → 5-Acetamido-6-benzoylindane

HRID 991514
ノート
印刷プレビュー

反応式

HRID 991514 の反応式
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>O.C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamideHCID 6451240Aluminum(III) Chloride2 回

生成物 1

HCID 235056145-Acetamido-6-benzoylindane収率 13%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-acetamidoindane (1.0 g, 5.7 mmol) and benzoyl chloride (732 mL, 6.3 mmol) in 15 mL, of CH2Cl2 at 0° C. was added AlCl3 (1.52 g, 11.4 mmol) as a solid. The mixture was stirred to rt overnight. A spatula full of AlCl3 was added and the mixture heated to reflux for 3 days. The solution was then poured into a mixture of concentrated HCl and ice, and stirred. The mixture was then diluted with water and extracted with 2×50 mL of CH2Cl2. The extract was washed with brine, then dried over MgSO4 and concentrated in vacuo. The crude residue was subjected to flash column chromatography eluting with EtOAc/hexane to give the title compound (200 mg. 13%). 1H NMR (CDCl3): 10.95 (s, 1H), 8.50 (s, 1H), 7.68 (d, 2H), 7.59 (t, 1H), 7.49 (t, 2H), 7.37 (s, 1H), 2.99 (t, 2H), 2.83 (t, 2H), 2.22 (s, 3H), 2.10 (p, 2H).

後処理

  1. temperaturethe mixture heated
  2. temperatureto reflux for 3 days
  3. stirringstirred
  4. extractionextracted with 2×50 mL of CH2Cl2
  5. washThe extract was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. washeluting with EtOAc/hexane

出典と根拠

ORDレコード
ord-13b548ca296946b4a4199cd6389e11c3
出典データセット
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06465472B1

反応ノート

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