Potassium Dichromate → 5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid

HRID 1274614

Reaktionsgleichung

Reaktionsgleichung von HRID 1274614
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:2].[K+].[K+].[CH3:12][N:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:16](=[O:23])[N:15]([C:24]2[CH:25]=[CH:26][C:27]3[S:31][N:30]=[C:29]([CH:32]=[O:33])[C:28]=3[CH:34]=2)[C:14]1=[O:35]>S(=O)(=O)(O)O.C(O)(=O)C.O>[CH3:12][N:13]1[C:18]([C:19]([F:20])([F:21])[F:22])=[CH:17][C:16](=[O:23])[N:15]([C:24]2[CH:25]=[CH:26][C:27]3[S:31][N:30]=[C:29]([C:32]([OH:2])=[O:33])[C:28]=3[CH:34]=2)[C:14]1=[O:35]

Komponenten

6

Edukt 2

HCID 24502Potassium DichromateHCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

Produkt 1

HCID 111878605-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acidAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of potassium dichromate (10.0 g) in 1.5 M sulfuric acid (200 mL) is cooled to 0° C., treated dropwise with a solution of a 2:3 mixture of 3-[3-(hydromethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione and 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (12.0 g) in acetic acid, stirred at room temperature for 2 hours, and diluted with water. The resultant aqueous mixture is extracted with methylene chloride. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a white solid (8.50 g, mp 149-152° C.).

Aufarbeitung

  1. extractionThe resultant aqueous mixture is extracted with methylene chloride
  2. washwashed sequentially with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-50cae551cddb4cf8ac54d8ea1354bcf1
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156700

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