3-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chloride → Isopyrazam

HRID 1803098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803098
[F:1][CH:2]([F:12])[C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[CH:13]([CH:16]1[CH:20]2[C:21]3[C:26]([CH:17]1[CH2:18][CH2:19]2)=[CH:25][CH:24]=[CH:23][C:22]=3[NH2:27])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[CH:13]([CH:16]1[CH:20]2[C:21]3[C:26]([CH:17]1[CH2:18][CH2:19]2)=[CH:25][CH:24]=[CH:23][C:22]=3[NH:27][C:8]([C:7]1[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=1)=[O:9])([CH3:15])[CH3:14]

Komponenten

4

Edukt 2

HCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 594313419-Isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-amine

Produkt 1

HCID 25271089Isopyrazam

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

15.1 g (0.0752 mol, 96.5% pure) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride were dissolved at 25° C. in 100 ml of toluene. The solution was evacuated to 350 mbar and heated to 85° C. Subsequently, within 60 min, 20 g (0.074 mol, 75%; 65:10 syn/anti isomer mixture) of 9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-ylamine, dissolved in 100 ml of toluene, were metered in and the reaction mixture was stirred for another 1 hour. After venting and cooling to 25° C., the mixture was stirred overnight. Subsequently, the mixture was concentrated under reduced pressure and dried. The yield was 31.3 g; according to 1H NMR 70% pure (82%).

Aufarbeitung

  1. customThe solution was evacuated to 350 mbar
  2. temperaturecooling to 25° C.
  3. stirringthe mixture was stirred overnight
  4. concentrationSubsequently, the mixture was concentrated under reduced pressure
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5caa2a9f753d4d1ca365d692eb890c5b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08350046B2

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