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

HRID 1921599노트

반응식

HRID 1921599 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8bed1aac83284df5af82b5f433d2ecdd
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173696B2

반응 노트

불러오는 중…