Thiochroman-4-one → 6-bromo-2,3-dihydrothiochromen-1,1-dioxide-4-one

HRID 1921599Notes

Reaction equation

HRID 1921599 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 431675396-bromo-2,3-dihydrothiochromen-1,1-dioxide-4-oneYield 33%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8bed1aac83284df5af82b5f433d2ecdd
Source dataset
uspto-grants-2012_05
Patent number
US08173696B2

Reaction notes

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