3-Methoxy-2-MethylBenzoic Acid → Methoxyfenozide

HRID 260807노트

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HRID 260807 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 105010Methoxyfenozide수율 57%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 24386Thionyl Chloride용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-5e034e0614824442aac77f969354f862
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05530028

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