Acetic Acid → Fomesafen

HRID 1164388

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HRID 1164388 반응식
N[C:2]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[Cl:26])=[CH:11][C:3]=1[C:4]([NH:6][S:7]([CH3:10])(=[O:9])=[O:8])=[O:5].C(O)(=O)C.[N+:31]([O-:34])(O)=[O:32].OO>O>[Cl:26][C:17]1[CH:18]=[C:19]([C:22]([F:23])([F:25])[F:24])[CH:20]=[CH:21][C:16]=1[O:15][C:12]1[CH:13]=[CH:14][C:2]([N+:31]([O-:34])=[O:32])=[C:3]([CH:11]=1)[C:4]([NH:6][S:7]([CH3:10])(=[O:8])=[O:9])=[O:5]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 944Nitric AcidHCID 12799631HCID 12799631, 화합물

생성물 1

HCID 51556Fomesafen

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

A stirred solution is prepared containing 39.5 g of 2-amino-5-(2-chloro-4-trifluoromethylphenoxy)-N-methanesulphonyl benzamide of the formula (V), R1 =methyl, 1380 ml of glacial acetic acid and 1.0 g of concentrated nitric acid at about 40° C. To the solution is added 138 g of a 30% by weight hydrogen peroxide in water solution and the reaction mixture is raised to and maintained at about 70° C. for 20 hours. The solution is then poured slowly into about 3 liters of ice water with precipitation of crude product. After filtration, the product is isolated as a solid, m.p. 175°-183° C., containing 68% of the compound of formula (I), R1 =methyl, as determined by high pressure liquid chromatography, thin layer chromatography and its mass spectrum. Recrystallization from aqueous methanol yields the product 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro-N-methanesulphonyl benzamide, m.p. 216°-218° C.

후처리

  1. customA stirred solution is prepared
  2. temperaturethe reaction mixture is raised to and
  3. filtrationAfter filtration
  4. customthe product is isolated as a solid, m.p. 175°-183° C.
  5. customRecrystallization from aqueous methanol

출처 및 근거

ORD 기록
ord-12889c89d49b4dbb9e6f10a14be5ec04
출처 데이터셋
uspto-grants-1983_01
특허 번호
US04369316

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