Hydrochloric Acid → N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]acetamide

HRID 1907817

반응식

HRID 1907817 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([S:17]([F:22])([F:21])([F:20])([F:19])[F:18])[CH:16]=1)[C:8](N(OC)C)=[O:9])(=[O:3])[CH3:2].[CH3:23][Si](C)(C)[N-][Si](C)(C)C.[Li+].COCCCC.C[Mg]Br.Cl>C1COCC1.C(OCC)(=O)C.O>[C:8]([C:7]1[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:16]=[C:15]([S:17]([F:22])([F:18])([F:20])([F:21])[F:19])[CH:14]=1)(=[O:9])[CH3:23]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 12338Butyl methyl etherHCID 2733832Lithium HexamethyldisilazideHCID 581368203-Acetylamino-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamideHCID 178418573HCID 178418573, 화합물2회

생성물 1

HCID 58136897N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]acetamide수율 82.3%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

3-Acetylamino-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide (1.2 g) was dissolved in absolute THF (30 ml) and stirred at 0° C. with lithium hexamethyldisilazide (721 μl; density: 0.8 g/1; 23% in tent-butyl methyl ether) for 30 min. At 0° C., methylmagnesium bromide (2.87 ml, 3 M in diethyl ether) was then added dropwise while stirring. After stirring at RT for 2.5 h, further methylmagnesium bromide (1 ml, 3 M in diethyl ether) was added and the mixture was stirred again for 2.5 h. For workup, 1 N hydrochloric acid was added dropwise while cooling with ice, followed by water and ethyl acetate. The organic phase was removed and the water phase was extracted twice more with ethyl acetate. The combined ethyl acetate phases were dried over sodium sulfate, filtered and concentrated. The crude product (1.03 g) was combined with a crude product prepared in the same way (75 mg) and purified using silica gel with dichloromethane-methanol as the eluent. 860 mg of the desired compound were obtained. LC-MS Rt: 1.34 min [M+H]+:304.0

후처리

  1. stirringAfter stirring at RT for 2.5 h
  2. stirringthe mixture was stirred again for 2.5 h
  3. temperaturewhile cooling with ice
  4. customThe organic phase was removed
  5. extractionthe water phase was extracted twice more with ethyl acetate
  6. dry with materialThe combined ethyl acetate phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customprepared in the same way (75 mg)
  10. custompurified

출처 및 근거

ORD 기록
ord-81db2774237e4d808272eb10944a914b
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598177B2

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