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Phenol → Phenyl 1-(4-Chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylate

HRID 67265
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 67265
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C:10]([C:16]([OH:18])=[O:17])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(O[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=O.C1(O)C=CC=CC=1>C1(C)C=CC=CC=1.CCCCCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C:10]([C:16]([O:18][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:17])=[N:9]2)=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 996PhenolHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 197225Fenridazon

Produkt 1

HCID 9192006Phenyl 1-(4-Chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylateAusbeute 19,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 1140TolueneLösungsmittel2×
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To an ice cooled suspension of 5.29 g (0.02 mol) 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic Acid (see Example 12) and 2.02 g (0.02 mol) of triethylamine in 125 mol of toluene there is added dropwise 3.13 g (0.02 mol) of phenyl chloroformate. The suspension formed is stirred at room temperature for 15 minutes and to it there is added 1.88 g (0.02 mol) of phenol in 25 ml of toluene. The mixture is stirred at room temperature for 18 hrs. and to it there is added 100 ml of water. The suspension is stirred at room temperature for 2 hrs. and is poured into 800 ml of hexane. The suspension formed is stirred at room temperature for 3 hrs. and is vacuum filtered. The filter cake is slurried in 25 ml of toluene and is filtered. The filtrate is added to 150 ml of hexane and the suspension formed is stirred at room temperature for 2 hrs. The suspension is vacuum filtered and the filter cake air dried to afford 1.3 g (19% yield) of product, mp 140°-146° C.

Aufarbeitung

  1. customThe suspension formed
  2. stirringThe mixture is stirred at room temperature for 18 hrs
  3. stirringThe suspension is stirred at room temperature for 2 hrs
  4. customThe suspension formed
  5. stirringis stirred at room temperature for 3 hrs
  6. filtrationfiltered
  7. filtrationis filtered
  8. additionThe filtrate is added to 150 ml of hexane
  9. customthe suspension formed
  10. stirringis stirred at room temperature for 2 hrs
  11. filtrationfiltered
  12. customthe filter cake air dried

Quellen und Nachweise

ORD-Eintrag
ord-e9b5717f5d59430f8f2ec1312dd35dfb
Quelldatensatz
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04345934

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