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Tetrahydrofuran → 2-(2-Amino-3-benzoylphenyl)-2-(methylsulfanyl)acetamide

HRID 1446819
ノート
印刷プレビュー

反応式

HRID 1446819 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].CC[C:18](N)=[S:19].[CH2:21]([N:23](CC)CC)[CH3:22].[O:28]1CCCC1>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:12][CH:13]=[CH:14][C:15]=1[CH:22]([S:19][CH3:18])[C:21]([NH2:23])=[O:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 760802-AminobenzophenoneHCID 2760628Propanethioamide

生成物 1

HCID 156347272-(2-Amino-3-benzoylphenyl)-2-(methylsulfanyl)acetamide収率 43%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a cold (-70° C.) solution of 19.7 g (0.10 mole of 2-amino-benzophenone in 300 ml of methylene chloride, under nitrogen atmosphere, was added a solution of 11.5 g (0.10 mole) of 95% t-butylpochlorite in 30 ml of methylene chloride followed after 10 min by a solution of 10.5 g (0.1 mole) of methylthioacetamide in 300 ml of tetrahydrofuran. The temperature was maintained at or below -55° C. during these additions. After one additional hour at -60° C. the mixture was allowed to warm to room temperature and the precipitate was collected by filtration. The precipitate was slurried in 200 ml of methylene chloride and 11 g (0.11 mole) of triethylamine was added. The mixture was stirred for 5 min. The solution was washed two times with 100 ml of water and the organic phase dried over magnesium sulfate and concentrated under reduced pressure. The residue was washed with diethylether and dried to yield 13.0 g (43%) of a light yellow powder, m.p. 153°-155° C.

後処理

  1. temperatureThe temperature was maintained at or below -55° C. during these additions
  2. customat -60° C.
  3. filtrationthe precipitate was collected by filtration
  4. washThe solution was washed two times with 100 ml of water
  5. dry with materialthe organic phase dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with diethylether
  8. customdried

出典と根拠

ORDレコード
ord-baed0f88b8a349f38eae5eeddd35a62d
出典データセット
uspto-grants-1982_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04313949

反応ノート

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