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Citric Acid → N-(6-Chloropyrimidin-4-yl)-4-isopropylbenzenesulfonamide

HRID 444971
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 444971
C([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH2:13])(=[O:12])=[O:11])(C)C.[H-].[Na+].[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[CH:19][N:18]=1.[C:24](O)(=O)[CH2:25][C:26](CC(O)=O)(C(O)=O)O>CS(C)=O.O>[Cl:16][C:17]1[N:18]=[CH:19][N:20]=[C:21]([NH:13][S:10]([C:5]2[CH:4]=[CH:9][C:8]([CH:25]([CH3:26])[CH3:24])=[CH:7][CH:6]=2)(=[O:11])=[O:12])[CH:22]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 190986352-(Propan-2-yl)benzene-1-sulfonamide

Produkt 1

HCID 86003781N-(6-Chloropyrimidin-4-yl)-4-isopropylbenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

996 mg (5.0 mmol) of isopropylbenzenesulfonamide were dissolved in 20 ml of dimethyl sulfoxide, after which 288 mg (6.0 mmol) of 50% sodium hydride were added and the mixture was stirred at room temperature for 30 minutes. 819 mg (5.5 mmol) of 4,6-dichloropyrimidine were then added and the reaction mixture was stirred overnight at room temperature. Subsequently, the mixture was heated at 90° C. for 3 hours and, after that, stirred at 120° C., in a microwave oven, for 30 minutes. After the reaction mixture had cooled down to room temperature, it was diluted with 150 ml of water, neutralized with citric acid and extracted three times with diethyl ether. The residue, which was obtained after drying with sodium sulfate and after removing the solvent, was dissolved in 100 ml of diethyl ether and extracted with an aqueous solution of sodium hydrogen carbonate. The aqueous phase was acidified and extracted with diethyl ether. The organic phase was dried, filtered and evaporated down to dryness, with 440 mg (28% of theory) of the title compound being obtained.

Aufarbeitung

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. temperatureSubsequently, the mixture was heated at 90° C. for 3 hours
  3. stirringafter that, stirred at 120° C., in a microwave oven, for 30 minutes
  4. temperatureAfter the reaction mixture had cooled down to room temperature
  5. extractionextracted three times with diethyl ether
  6. customThe residue, which was obtained
  7. dry with materialafter drying with sodium sulfate
  8. customafter removing the solvent
  9. dissolutionwas dissolved in 100 ml of diethyl ether
  10. extractionextracted with an aqueous solution of sodium hydrogen carbonate
  11. extractionextracted with diethyl ether
  12. customThe organic phase was dried
  13. filtrationfiltered
  14. customevaporated down to dryness, with 440 mg (28% of theory) of the title compound
  15. custombeing obtained

Quellen und Nachweise

ORD-Eintrag
ord-dfa2273311654974a37394abd54d0579
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08476275B2

Notizen zur Reaktion

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