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1-Bromo-3-methylbutan-2-one → HCID 57666787, Verbindung

HRID 1445412
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1445412
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[S:7])([O-:3])=[O:2].Br[CH2:18][C:19](=O)[CH:20]([CH3:22])[CH3:21]>O1CCOCC1>[CH:20]([C:19]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:14])[F:15])=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[S:7][CH:18]=1)([CH3:22])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 108990371-Bromo-3-methylbutan-2-oneHCID 576668062-Nitro-4-(trifluoromethyl)benzenecarbothioamide

Produkt 1

HCID 57666787HCID 57666787, VerbindungAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Nitro-4-trifluoromethyl-thiobenzamide (55), (100 mg, 0.4 mmol) was dissolved in dioxan (4 ml) in a 10 ml test tube and to this solution was added 1-bromo-3-methyl-butan-2-one (52) (72.6 mg, 0.44 mmol). A stirrbar was added and the tube was sealed and heated to 100° C. over night. After cooling to ambient temperature, the vessel was de-capped, the solvent removed in vacuo and the residue partitioned between DCM and 10% aqueous NaHCO3 solution. The organic phase was separated and washed with additional 10% aqueous NaHCO3 solution and brine. The organic phase was filtered through a hydrophobic frit and the solvent removed in vacuo which gave the target compound (120 mg, 90%). LC/MS: (Method I): tR=2.26 min, >90%, m/z (ESI)=317 (MH+).

Aufarbeitung

  1. additionA stirrbar was added
  2. customthe tube was sealed
  3. temperatureAfter cooling to ambient temperature
  4. customthe solvent removed in vacuo
  5. customthe residue partitioned between DCM and 10% aqueous NaHCO3 solution
  6. customThe organic phase was separated
  7. washwashed with additional 10% aqueous NaHCO3 solution and brine
  8. filtrationThe organic phase was filtered through a hydrophobic frit
  9. customthe solvent removed in vacuo which

Quellen und Nachweise

ORD-Eintrag
ord-dcd1f01dd6d5473ba3c9df6331e6959e
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07666834B2

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