2,6-Dichlorobenzoic acid → 2-(2,6-Dichlorophenylcarbonyloxymethyl)-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743462
Cl[CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][C:11]([CH3:14])([Cl:13])[CH3:12])[N:5]([CH3:15])[S:4]1(=[O:17])=[O:16].[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:20]=1[C:21]([OH:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:20]=1[C:21]([O:23][CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][C:11]([CH3:14])([Cl:13])[CH3:12])[N:5]([CH3:15])[S:4]1(=[O:17])=[O:16])=[O:22]

Komponenten

5

Edukt 3

HCID 57582,6-Dichlorobenzoic acidHCID 11430Potassium CarbonateHCID 194244092-Chloromethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Produkt 1

HCID 158380732-(2,6-Dichlorophenylcarbonyloxymethyl)-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-chloromethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.41 g; 1.35 mmol) in DMF was added at room temperature 2,6-dichlorobenzoic acid (0.283 g; 1.48 mmol) and potassium carbonate (0.246 g, 1.78 mmol), and the resulting solution was allowed to react at room temperature for 40 hours. The mixture was poured into ice/water, extracted with ethyl acetate, and the organic layer was washed with water, brine, and dried. The organic solution was concentrated in vacuo and the residue was purified by silica column chromatography to afford 62 mg (10%) of 2-(2,6-dichlorophenylcarbonyloxymethyl) -4- (3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: Ar=2, 6-Cl2 -phenyl; R1 =H; R2 =(CH2)2C (Cl) (CH3)2 ; R3 =CH3) as a gum.

Aufarbeitung

  1. customto react at room temperature for 40 hours
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water, brine
  4. customdried
  5. concentrationThe organic solution was concentrated in vacuo
  6. customthe residue was purified by silica column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f789ba525fee4e3baaa68f24897a265c
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556909

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