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

HRID 217765

Reaktionsgleichung

Reaktionsgleichung von HRID 217765
[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]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 12338Butyl methyl etherHCID 2733832Lithium HexamethyldisilazideHCID 581368203-Acetylamino-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamideHCID 178418573HCID 178418573, Verbindung2×

Produkt 1

HCID 58136897N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]acetamideAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f90fa3b364a84c5c8341bf3f83431a2c
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198272B2

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