Hydrochloric Acid → Fomesafen

HRID 638660

反応式

HRID 638660 の反応式
[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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 44073AcifluorfenHCID 72879Methanesulfonamide

生成物 1

HCID 51556Fomesafen

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ac5c4398a2ad444992c2ed1ab2d30a7d
出典データセット
uspto-grants-1985_12
特許番号
US04562279

関連ノート

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