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Triethylamine → HCID 178428868、化合物

HRID 434214
ノート
印刷プレビュー

反応式

HRID 434214 の反応式
Br[C:2]1[C:3]([CH3:17])=[C:4]([C:12]2[CH2:16][CH2:15][O:14][N:13]=2)[C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:18][N:19]1[C:23]([OH:24])=[CH:22][CH:21]=[N:20]1.[C:25](=O)([O-])[O-:26].[K+].[K+].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH3:18][N:19]1[C:23]([OH:24])=[C:22]([C:25](=[O:26])[C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([C:12]3[CH2:16][CH2:15][O:14][N:13]=3)[C:3]=2[CH3:17])[CH:21]=[N:20]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 109470753-(3-Bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazoleHCID 178481816HCID 178481816、化合物

生成物 1

HCID 178428868HCID 178428868、化合物収率 11.1%

試薬・触媒・溶媒 2

HCID 178418476
HCID 178418476、化合物
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
130 °C

実験手順

2.2 1 of 1,4-dioxane, 100 g (0.315 mol) of 3-(3-bromo-2-methyl-6-methylsulfonylphenyl)-4,5-dihydroisoxazole, 30.82 g (0.315 mol) of 1-methyl-5-hydroxypyrazole, 87 g (0.63 mol) of potassium carbonate, 63.5 g (0.63 mol) of triethylamine and 11.2 g (0.016 mol) of bis(triphenylphosphine)-palladium dichloride were added to a 3.5 l autoclave. The autoclave was then flushed twice with nitrogen, a carbon monoxide pressure of 10 kg/cm2 was applied and the mixture was heated with stirring to 130° C. The carbon monoxide pressure was increased to 20 kg/cm2 and the mixture was stirred at 130° C. for 24 h. The mixture was then concentrated under reduced pressure and the residue was taken up in water. The aqueous phase of pH 11 was extracted with dichloromethane. The organic phase is discarded. The aqueous phase is adjusted to pH 4 using 18% strength hydrochloric acid. The precipitate was filtered off, washed three times with water and dried at 40° C. under reduced pressure. This gives 85 g of product. The filtrate is extracted with dichloromethane. The organic phase is dried with sodium sulfate, and the solvent is then removed under reduced pressure, giving a further 12.7 g of product.

後処理

  1. customThe autoclave was then flushed twice with nitrogen
  2. temperaturethe mixture was heated
  3. temperatureThe carbon monoxide pressure was increased to 20 kg/cm2
  4. stirringthe mixture was stirred at 130° C. for 24 h
  5. concentrationThe mixture was then concentrated under reduced pressure
  6. extractionThe aqueous phase of pH 11 was extracted with dichloromethane
  7. filtrationThe precipitate was filtered off
  8. washwashed three times with water
  9. customdried at 40° C. under reduced pressure
  10. extractionThe filtrate is extracted with dichloromethane
  11. dry with materialThe organic phase is dried with sodium sulfate
  12. customthe solvent is then removed under reduced pressure

出典と根拠

ORDレコード
ord-9a8f131dd63d481abb09145d7effc1fa
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06670482B2

反応ノート

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