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

HRID 1921599ノート

反応式

HRID 1921599 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8bed1aac83284df5af82b5f433d2ecdd
出典データセット
uspto-grants-2012_05
特許番号
US08173696B2

反応ノート

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