Thiochroman-4-one → 6-bromo-3,4-dihydro-2H-1lambda6-benzothiopyran-1,1,4-trione

HRID 1921599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921599
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8](=[O:13])(=[O:12])[CH2:7][CH2:6][C:5]2=NNC(N)=S.S1C2C(=CC=CC=2)C(=[O:29])CC1.NNC(N)=S>CC1C=CC(S(O)(=O)=O)=CC=1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8](=[O:13])(=[O:12])[CH2:7][CH2:6][C:5]2=[O:29]

Komponenten

6

Edukt 3

HCID 19048Thiochroman-4-oneHCID 2723789ThiosemicarbazideHCID 732295466-Bromo-1,1-dioxo-1-thiochroman-4-one thiosemicarbazone

Produkt 1

HCID 431675396-bromo-3,4-dihydro-2H-1lambda6-benzothiopyran-1,1,4-trioneAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

6-Bromo-1,1-dioxo-1-thiochroman-4-one thiosemicarbazone (23) Into a round bottom flask containing 0.198 g of the appropriate thiochroman-4-one (0.147 g, 0.534 mmol), 10 mL of anhydrous methanol were added and the solution was refluxed for about 15 minutes before adding thiosemicarbazide (0.0598 g, 0.657 mmol) and 1.4 mg of TsOH. After the reaction mixture was refluxed under nitrogen atmosphere for 10 h, a solid was formed which was filtered and, then purified by column chromatography (30% EtOAc/70% hex). 0.0618 g (0.178 mmol) of the product was obtained in a 33% yield.

Aufarbeitung

  1. additionwere added
  2. temperaturethe solution was refluxed for about 15 minutes
  3. temperatureAfter the reaction mixture was refluxed under nitrogen atmosphere for 10 h
  4. customa solid was formed which
  5. filtrationwas filtered
  6. custompurified by column chromatography (30% EtOAc/70% hex)

Quellen und Nachweise

ORD-Eintrag
ord-8bed1aac83284df5af82b5f433d2ecdd
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173696B2

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