Hydrochloric Acid → Fomesafen

HRID 638660

반응식

HRID 638660 반응식
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](O)=[O:11].[CH3:25][S:26]([NH2:29])(=[O:28])=[O:27].Cl>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([NH:29][S:26]([CH3:25])(=[O:28])=[O:27])=[O:11]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 44073AcifluorfenHCID 72879Methanesulfonamide

생성물 1

HCID 51556Fomesafen

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

반응 조건

온도
110 °C

실험 절차

5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid (2 gm) is heated under reflux in excess of thionyl chloride (20 ml) for 90 minutes. The excess thionyl chloride is removed under vacuum. The residual product is mixed with at least 1.5 mole equivalent CH3SO2NH2, heated slowly in an oil bath to about 110° C. The reaction temperature is slowly raised to about 150° C. and kept at that temperature for at least 30 minutes or till the HCl ceases to evolve. The reaction mixture is cooled and the residue is crystallized from isopropanol to give 5-(2chloro-4-trifluoromethylphenoxy)-2-nitro-N-methansulphonyl benzamide, m.p. 201° C. In a similar way, but using the appropriate sulphonamide in place of methanesulphonamide, the corresponding nitrobenzoic acid sulphonamides are obtained, giving the following melting points 162° C., 179° C., 185° C., 170° C., 101° C., from the reaction with ethyl, propyl, butyl, hexyl and trifluoromethanesulphonamide respectively.

후처리

  1. customThe excess thionyl chloride is removed under vacuum
  2. temperatureThe reaction temperature is slowly raised to about 150° C.
  3. temperatureThe reaction mixture is cooled
  4. customthe residue is crystallized from isopropanol

출처 및 근거

ORD 기록
ord-ac5c4398a2ad444992c2ed1ab2d30a7d
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04562279

연결된 노트

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