4-Chlorobenzenesulfonamide → 1,1-Dimethylethyl 4-[(4-chlorophenyl)sulfonylaminocarbonyl]benzoate

HRID 326537

Reaktionsgleichung

Reaktionsgleichung von HRID 326537
[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.ClCCl>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:27][C:11]([C:10]2[CH:9]=[CH:8][C:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:16])=[CH:15][CH:14]=2)=[O:13])(=[O:25])=[O:26])=[CH:22][CH:23]=1

Komponenten

5

Edukt 2

HCID 668244-ChlorobenzenesulfonamideHCID 27609544-(tert-Butoxycarbonyl)benzoic acid

Produkt 1

HCID 545475071,1-Dimethylethyl 4-[(4-chlorophenyl)sulfonylaminocarbonyl]benzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 5-liter, 3-necked, round-bottomed flask was equipped with a mechanical stirrer and nitrogen inlet. dichloromethane (2 liters) was placed in the reaction flask and terephthalic acid mono-t-butyl ester (127.5 g), 4-dimethylaminopyridine (70.06 g), and 4-chlorobenzenesulfonamide (110.04 g) were added in that order using dichloromethane (400 ml) to wash down the solids. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (110.10 g) was added in portions over 10 min using dichloromethane (100 ml) to wash down the solid. After the reaction mixture was stirred overnight at room temperature, it was evaporated. The residue was partitioned between ethyl acetate and water. The organic solution was washed (20% (w/v) aqueous citric acid, saturated aqueous NaHCO3, brine), dried (Na2SO4), and evaporated to a white solid. After drying in a vacuum oven at 50° C., the ester (227 g, 100%) was obtained in a sufficiently pure state to be used directly for the next step; TLC, Rf =0.43, methanol:chloroform (15:85). (Further purification was possible by recrystallization from ethanol:water; mp above 300° C.).

Aufarbeitung

  1. customA 5-liter, 3-necked, round-bottomed flask was equipped with a mechanical stirrer and nitrogen inlet
  2. additionwere added in that order
  3. washto wash down the solids
  4. addition1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (110.10 g) was added in portions over 10 min
  5. washto wash down the solid
  6. customit was evaporated
  7. customThe residue was partitioned between ethyl acetate and water
  8. washThe organic solution was washed (20% (w/v) aqueous citric acid, saturated aqueous NaHCO3, brine)
  9. dry with materialdried (Na2SO4)
  10. customevaporated to a white solid
  11. customAfter drying in a vacuum oven at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-e0ae08786bf7476dabbf90b42b253d04
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270301

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