3-Methoxy-2-MethylBenzoic Acid → Methoxyfenozide

HRID 260807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 260807
[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[CH3:13][C:14]1[CH:15]=[C:16]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[C:17]([N:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[NH2:20])=[O:18]>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:20][N:19]([C:17](=[O:18])[C:16]1[CH:15]=[C:14]([CH3:13])[CH:27]=[C:26]([CH3:28])[CH:25]=1)[C:21]([CH3:24])([CH3:23])[CH3:22])=[O:8]

Komponenten

5

Edukt 2

HCID 70214833-Methoxy-2-MethylBenzoic AcidHCID 10878689N-tert-Butyl-3,5-dimethylbenzohydrazide

Produkt 1

HCID 105010MethoxyfenozideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of 3-methoxy-2-methylbenzoic acid (1.5 g, 0.01 mole) in thionyl chloride (10 mL.) was refluxed for 45 minutes and then stripped under reduced pressure. The residue was dissolved in methylene chloride (50 mL) and added dropwise with cooling at 0° C. to a solution of N-(3,5-dimethylbenzoyl)-N-tert-butylhydrazine (4.4 g. 0.02 mole) in methylene chloride (50 mL). Following the addition, the solution was stirred overnight at room temperature and filtered. The filter-cake was washed extensively with water and ether, and then dried in vacuo to give 2.1 g of N-(3-methoxy-2-methylbenzoyl)-N'-(3,5-dimethylbenzoyl)-N'-tert-butylhydrazine, melting at 204°-204.5° C. 1H-NMR δppm 1.50 (s, 9H, tert-Bu), 1.63 (s, 3H, Ar--CH3), 2.25 (s, 6H, di--CH3) 3.75 (s, 3H, OCH3), 6.26 (d, 1H, Ar), 6.93-7.20 (m, 5H, Ar).

Aufarbeitung

  1. additionadded dropwise
  2. additionthe addition
  3. filtrationfiltered
  4. washThe filter-cake was washed extensively with water and ether
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5e034e0614824442aac77f969354f862
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530028

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