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Sulfuric Acid → 1-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanone

HRID 1258519
ノート
印刷プレビュー

反応式

HRID 1258519 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([NH:16]C(=O)C(F)(F)F)[CH:7]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:9]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)O>O.C(#N)C>[NH2:16][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[C:8]([S:10]([F:15])([F:11])([F:12])([F:13])[F:14])[CH:7]=1
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 2

HCID 1118Sulfuric Acid2 回HCID 58085708HCID 58085708、化合物

生成物 1

HCID 581368521-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanone収率 86.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
75 °C

実験手順

N-(3-Acetyl-5-pentafluorosulfanylphenyl)-2,2,2-trifluoroacetamide (4 g, for preparation see example 4d) was suspended in 6 ml of water and 12 ml of acetonitrile, and 6 ml of concentrated sulfuric acid were added dropwise to this suspension. After stirring at 75° C. for 4 h and leaving to stand at RT overnight, the reaction was completed by adding another 2 ml of concentrated sulfuric acid and heating the mixture at 75° C. for 3 h. The reaction mixture was poured onto ice-water and extracted with ethyl acetate. The ethyl acetate phase was washed to neutrality with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by means of chromatography on silica gel. The product-containing fractions were combined and the solvent (heptane/ethyl acetate) was concentrated under reduced pressure. 2.53 g of 1-[3-amino-5-(pentafluorosulfanyl)phenyl]ethanone were obtained.

後処理

  1. customleaving
  2. waitto stand at RT overnight
  3. temperatureheating the mixture at 75° C. for 3 h
  4. additionThe reaction mixture was poured onto ice-water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate phase was washed to neutrality with saturated sodium hydrogencarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by means of chromatography on silica gel
  11. concentrationthe solvent (heptane/ethyl acetate) was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-598badac10e94cdc968260e0e07a30b1
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08466169B2

反応ノート

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