Bentazon → 1-[5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl]-3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide

HRID 1759297

Reaktionsgleichung

Reaktionsgleichung von HRID 1759297
[CH:1]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[NH:6][S:5]1(=[O:16])=[O:15])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:19]=1[O:20][C:21]1[CH:22]=[CH:23][C:24]([N+:30]([O-:32])=[O:31])=[C:25]([CH:29]=1)[C:26](Cl)=[O:27]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:17][C:18]1[CH:36]=[C:35]([C:37]([F:38])([F:40])[F:39])[CH:34]=[CH:33][C:19]=1[O:20][C:21]1[CH:22]=[CH:23][C:24]([N+:30]([O-:32])=[O:31])=[C:25]([CH:29]=1)[C:26]([N:6]1[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[S:5]1(=[O:15])=[O:16])=[O:27]

Komponenten

5

Edukt 2

HCID 2328BentazonHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Produkt 1

HCID 130379681-[5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl]-3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide (2.4 g, 0.01 mole) and tricthylamine (1.1 g, 0.011 mole) in a mixture of toluene (100 ml) and chloroform (100 ml) was added 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (3.8 g, 0.01 mole). The reaction was heated for 24 hours and then the solvent was removed. The residue was taken back up into chloroform and extracted three times with sodium hydroxide and finally with water. The organic solution was dried and evaporated to give 2.8 g of an oil which was triturated with petroleum ether to give a solid which was recrystallized from chloroform-petroleum ether to give a white solid, mp 125°-8° C.

Aufarbeitung

  1. temperatureThe reaction was heated for 24 hours
  2. customthe solvent was removed
  3. extractionextracted three times with sodium hydroxide
  4. customThe organic solution was dried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-eedcf819f34b4f90832152afe797dadd
Quelldatensatz
uspto-grants-1982_07
Patentnummer
US04340417

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