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Triethylamine → N'-(6-Chloro-5-(trimethylsilyl)pyridazin-3-yl)-2-fluorobenzohydrazide

HRID 1887032
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1887032
[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:12][NH2:13])=[CH:6][C:7]=1[Si:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[F:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>C(OCC)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:12][NH:13][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[F:21])=[CH:6][C:7]=1[Si:8]([CH3:9])([CH3:10])[CH3:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 154861653-Chloro-6-hydrazinyl-4-(trimethylsilyl)pyridazine

Produkt 1

HCID 15486174N'-(6-Chloro-5-(trimethylsilyl)pyridazin-3-yl)-2-fluorobenzohydrazideAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 21 (6.45 g, 30 mmol) and triethylamine (5 mL, 36 mmol) in diethyl ether (120 mL) was cooled to 0-5° C. in an ice bath. 2-Fluorobenzoyl chloride (4.8 g, 30 mmol) was added dropwise keeping the temperature less than 5° C. The reaction was stirred 30 min then quenched by the addition of anhydrous MeOH (0.4 mL). The mixture was diluted with hexane (100 mL) and filtered. The solids were washed with ether (2×15 mL), then water (30 mL). The solids were dissolved in dichloromethane (100 mL) with a small amount of MeOH to aid solubility, then washed with brine. The organic solution was dried over Na2SO4 and concentrated to give a 51.7% yield of 22 as a brownish solid.

Aufarbeitung

  1. customthe temperature less than 5° C
  2. customthen quenched by the addition of anhydrous MeOH (0.4 mL)
  3. additionThe mixture was diluted with hexane (100 mL)
  4. filtrationfiltered
  5. washThe solids were washed with ether (2×15 mL)
  6. dissolutionThe solids were dissolved in dichloromethane (100 mL) with a small amount of MeOH
  7. washwashed with brine
  8. dry with materialThe organic solution was dried over Na2SO4
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d34fd1bb6e3b4b41853a117f9f75731a
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501738B2

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