Water → 1-Methoxycarbonyl-4-chloro-3-(3,5-dichlorophenyl)pyrazole

HRID 1586368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586368
C(N(CC)CC)C.[Cl:8][C:9]1[C:10]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)=[N:11][NH:12][CH:13]=1.Cl[C:23]([O:25][CH3:26])=[O:24].O>CN(C)C1C=CN=CC=1.C1COCC1>[CH3:26][O:25][C:23]([N:12]1[CH:13]=[C:9]([Cl:8])[C:10]([C:14]2[CH:15]=[C:16]([Cl:21])[CH:17]=[C:18]([Cl:20])[CH:19]=2)=[N:11]1)=[O:24]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178478181HCID 178478181, Verbindung

Produkt 1

HCID 218526441-Methoxycarbonyl-4-chloro-3-(3,5-dichlorophenyl)pyrazoleAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2.52 g (0.0204 mol) of 4-dimethylaminopyridine and 18.3 ml (0.132 mol) of triethylamine are added to 30.55 g (0.12 mol) of 4-chloro-3-(3,5-dichlorophenyl)pyrazole dissolved in 300 ml of THF. A solution of 12.5 g (0.132 mol) of methyl chloroformate in 100 ml of THF is run, dropwise and at 0° C., into this solution. Stirring is continued for 20 h at room temperature. The reaction mixture is poured into 500 ml of water and extracted with ethyl acetate. After drying the organic phase and concentration under vacuum, the residue is triturated with 150 ml of heptane, filtered and dried. We obtain 33.5 g of 1-methoxycarbonyl-4-chloro-3-(3,5-dichlorophenyl)pyrazole, melting at 144° C.

Aufarbeitung

  1. customat 0° C.
  2. extractionextracted with ethyl acetate
  3. customAfter drying
  4. concentrationthe organic phase and concentration under vacuum
  5. customthe residue is triturated with 150 ml of heptane
  6. filtrationfiltered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ceef507936c2482a9ec32ee7aa5c9d9e
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05945382

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