3-Methoxy-2-MethylBenzoic Acid → Methoxyfenozide

HRID 260807Notes

Reaction equation

HRID 260807 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 105010MethoxyfenozideYield 57%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-5e034e0614824442aac77f969354f862
Source dataset
uspto-grants-1996_06
Patent number
US05530028

Reaction notes

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