p-Toluenesulfonic acid → HCID 57691414、化合物

HRID 548595

反応式

HRID 548595 の反応式
[CH2:1]([CH2:5][C:6](=O)[CH3:7])[C:2]([CH3:4])=O.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]#[N:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:4][C:2]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]#[N:18])[C:6]([CH3:7])=[CH:5][CH:1]=1

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 80352,5-Hexanedione2 回HCID 76307Phenylglycine nitrile

生成物 1

HCID 57691414HCID 57691414、化合物収率 102.1%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

反応条件

温度
155 °C

実験手順

p-Toluenesulfonic acid (2 mg, 0.16 mmol) and acetonylacetone (2.14 g, 18.7 mmol) were added sequentially to a solution of 2-aminophenylacetonitrile (2.06 g, 15.6 mmol) in toluene (30 mL). The reaction mixture was heated in an oil bath at 155° C. for 1 hour and then allowed to stand at ambient temperature overnight. Acetonylacetone (0.5 mL) and a small amount of p-toluenesulfonic acid were added and the reaction mixture was heated at reflux for 4 hours. The toluene layer was washed sequentially with saturated sodium bicarbonate and water (×2), dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to a dark oil. The oil was purified by prep HPLC (AnaLogix, eluted with a gradient of 10-30% ethyl acetate in hexanes) to provide 3.35 g of 2-(2,5-dimethylpyrrol-1-yl)phenylacetonitrile as a pale brown oil.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. washThe toluene layer was washed sequentially with saturated sodium bicarbonate and water (×2)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a dark oil
  7. customThe oil was purified by prep HPLC (AnaLogix
  8. washeluted with a gradient of 10-30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-b40475f78fa44b38b242a1e3a0993b80
出典データセット
uspto-grants-2011_05
特許番号
US07943610B2

関連ノート

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