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Benzenesulfonamide → 4-[14-(Trimethylsilyl)tetradecylamino]-N-(phenylsulfonyl)benzamide

HRID 652033
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 652033
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:13][Si:14]([CH3:40])([CH3:39])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.S(Cl)(Cl)=O>C(COC)OC.C(Cl)Cl.CC(N(C)C)=O>[CH3:40][Si:14]([CH3:13])([CH3:39])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]1[CH:31]=[CH:32][C:33]([C:34]([NH:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[O:35])=[CH:37][CH:38]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 7370BenzenesulfonamideHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 138848624-[14-(Trimethylsilyl)tetradecylamino)benzoic acid

Produkt 1

HCID 201983154-[14-(Trimethylsilyl)tetradecylamino]-N-(phenylsulfonyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344
Dichloromethane
Lösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

A solution of 30.7 g. of benzenesulfonamide in 250 ml. of dry dimethylacetamide is added dropwise, with stirring and cooling, to a suspension of 5.4 g. of sodium hydride in 100 ml. of dry dimethylacetamide during 30 minutes at room temperature. Stirring is continued for 30 minutes. In the meantime, a mixture of 36.2 g. of 4-[14-(trimethylsilyl)tetradecylamino] benzoic acid in 100 ml. of methylene chloride, 300 ml. of dimethoxyethane, and 40 ml. of thionyl chloride is refluxed for 1 hour and 15 minutes. The solution is evaporated and to the resulting oil residue is added, in one portion, the previously prepared mixture of sodium benzenesulfonamide in dimethylacetamide. The mixture is stirred for 30 minutes and then filtered. The filtrate is poured into 2 liters of water and 250 ml. of saturated sodium chloride solution. The product is collected by filtration and then dissolved in methylene chloride, the mixture is filtered through diatomaceous earth, and brine is added. The layers are separated, the organic phase is dried and evaporated. The residue is crystallized to yield the product as a white solid.

Aufarbeitung

  1. temperaturecooling, to a suspension of 5.4 g
  2. stirringStirring
  3. additionIn the meantime, a mixture of 36.2 g
  4. customThe solution is evaporated and to the resulting oil residue
  5. additionis added, in one portion
  6. additionthe previously prepared mixture of sodium benzenesulfonamide in dimethylacetamide
  7. stirringThe mixture is stirred for 30 minutes
  8. filtrationfiltered
  9. additionThe filtrate is poured into 2 liters of water and 250 ml
  10. filtrationThe product is collected by filtration
  11. dissolutiondissolved in methylene chloride
  12. filtrationthe mixture is filtered through diatomaceous earth, and brine
  13. additionis added
  14. customThe layers are separated
  15. customthe organic phase is dried
  16. customevaporated
  17. customThe residue is crystallized

Quellen und Nachweise

ORD-Eintrag
ord-27a271ea3bd149c29eff88593d54b0c2
Quelldatensatz
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04670421

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