3-Methoxy-2-MethylBenzoic Acid → Methoxyfenozide

HRID 260807ノート

反応式

HRID 260807 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 105010Methoxyfenozide収率 57%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 24386Thionyl Chloride溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5e034e0614824442aac77f969354f862
出典データセット
uspto-grants-1996_06
特許番号
US05530028

反応ノート

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