3,N-Dimethoxy-N-methyl-5-(pentafluorosulfanyl)benzamide → 1-[3-Methoxy-5-(pentafluorosulfanyl)phenyl]ethanone

HRID 532370ノート

反応式

HRID 532370 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([S:15]([F:20])([F:19])([F:18])([F:17])[F:16])[CH:14]=1)[C:6](N(OC)C)=[O:7].[CH3:21][Mg]Br>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH3:21])[CH:12]=[C:13]([S:15]([F:17])([F:20])([F:19])([F:16])[F:18])[CH:14]=1

参加物

4

反応物 2

HCID 581369683,N-Dimethoxy-N-methyl-5-(pentafluorosulfanyl)benzamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 441831181-[3-Methoxy-5-(pentafluorosulfanyl)phenyl]ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3,N-Dimethoxy-N-methyl-5-(pentafluorosulfanyl)benzamide (O3.007; 2.0 g) was dissolved in absolute THF (60 ml), and methylmagnesium bromide (5.2 ml, 3 M in diethyl ether) was added dropwise at 0° C. while stirring. After addition, the ice bath was removed and the mixture was stirred at RT for 2 h. 1 N hydrochloric acid was then added dropwise while cooling, followed by water and ethyl acetate. The organic phase was removed and the aqueous phase was extracted twice more with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC (met. A). The product-containing fractions were combined, freed of the acetonitrile and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 1.63 g of the desired compound were obtained.

後処理

  1. additionAfter addition
  2. customthe ice bath was removed
  3. stirringthe mixture was stirred at RT for 2 h
  4. addition1 N hydrochloric acid was then added dropwise
  5. temperaturewhile cooling
  6. customThe organic phase was removed
  7. extractionthe aqueous phase was extracted twice more with ethyl acetate
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by means of preparative HPLC (
  12. extractionextracted three times with ethyl acetate
  13. dry with materialThe combined extracts were dried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated

出典と根拠

ORDレコード
ord-f051fb360b164f33bc4a2024af60d782
出典データセット
uspto-grants-2014_10
特許番号
US08853206B2

反応ノート

読み込み中…