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

HRID 532370노트

반응식

HRID 532370 반응식
[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

참가 물질

4

반응물 2

HCID 581369683,N-Dimethoxy-N-methyl-5-(pentafluorosulfanyl)benzamideHCID 178418573HCID 178418573, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f051fb360b164f33bc4a2024af60d782
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853206B2

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