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Water → 2-t-butyl-4-methyl-5-(p-phenyl-benzylthio)-3(2H)-pyridazinone

HRID 2352019
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2352019
[H-].[Na+].[C:3]1([C:9]2[CH:16]=[CH:15][C:12]([CH2:13][SH:14])=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17]([N:21]1[C:26](=[O:27])[C:25]([CH3:28])=[C:24](Cl)[CH:23]=[N:22]1)([CH3:20])([CH3:19])[CH3:18].O>CN(C)C=O>[C:17]([N:21]1[C:26](=[O:27])[C:25]([CH3:28])=[C:24]([S:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:16][CH:15]=2)[CH:23]=[N:22]1)([CH3:20])([CH3:18])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 138222642-tert-butyl-5-chloro-4-methylpyridazin-3-(2H)-oneHCID 15147117(1,1'-Biphenyl)-4-methanethiol

Produkt 1

HCID 138250992-t-butyl-4-methyl-5-(p-phenyl-benzylthio)-3(2H)-pyridazinoneAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
3×

Versuchsvorschrift

To 10 ml of dry N,N-dimethylformamide was added 0.75 g of 55% sodium hydride. The resulting mixture was kept at 0° C. and added dropwise with a solution of 3.2 g of p-phenylbenzyl mercaptan dissolved in 15 ml of N,N-dimethylformamide. After ten minutes passed, the resulting mixture was added dropwise with a solution of 3.2 g of 2-t-butyl-5-chloro-4-methyl-3(2H)-pyridazinone dissolved in 15 ml of N,N-dimethylformamide. After completion of dropwise addition, the resulting mixture was reacted at 80° C. for one hour. The resulting solution was poured into 50 ml of water and extracted twice with 50 ml of diethyl ether. The resulting organic layer was dried over anhydrous sodium sulfate, and freed of solvent by distillation under reduced pressure to give 4.8 g of crude product. The crude product was recrystallized from 5 ml of hexane to obtain 2.6 g of 2-t-butyl-4-methyl-5-(p-phenyl-benzylthio)-3(2H)-pyridazinone.

Aufarbeitung

  1. customwas kept at 0° C.
  2. waitAfter ten minutes passed
  3. additionAfter completion of dropwise addition
  4. customthe resulting mixture was reacted at 80° C. for one hour
  5. extractionextracted twice with 50 ml of diethyl ether
  6. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  7. distillationfreed of solvent by distillation under reduced pressure
  8. customto give 4.8 g of crude product
  9. customThe crude product was recrystallized from 5 ml of hexane

Quellen und Nachweise

ORD-Eintrag
ord-d012267afa3a4c9bba7012298758936d
Quelldatensatz
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04874861

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