Diethyl squarate → 6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide

HRID 516911

Reaktionsgleichung

Reaktionsgleichung von HRID 516911
C(O[C:4]1[C:5](=[O:12])[C:6](=[O:11])[C:7]=1[O:8][CH2:9][CH3:10])C.[NH2:13][C:14]1[C:15]([OH:28])=[C:16]([S:21]([N:24]([O:26][CH3:27])[CH3:25])(=[O:23])=[O:22])[C:17]([Cl:20])=[CH:18][CH:19]=1>C(O)C>[Cl:20][C:17]1[C:16]([S:21]([N:24]([O:26][CH3:27])[CH3:25])(=[O:22])=[O:23])=[C:15]([OH:28])[C:14]([NH:13][C:4]2[C:5](=[O:12])[C:6](=[O:11])[C:7]=2[O:8][CH2:9][CH3:10])=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 123228Diethyl squarateHCID 183734833-Amino-6-chloro-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide

Produkt 1

HCID 568442936-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (2.83 g, 1.2 equiv) in ethanol (30 ml) was treated with TEA (1.54 g, 1.1 equiv) and the reaction mixture was heated to 45° C. 3-Amino-6-chloro-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide (3.7 g, 1 equiv) was added portion wise over 30 minutes, with vigorous stirring, maintaining the reaction mixture at 45° C. The reaction mixture was stirred at 45° C. for 1 hour and then allowed to cool to RT. The solvent was removed in vacuo and the residue was partitioned between EtOAc (600 ml) and water (2×200 ml). The aqueous portion was separated and extracted with EtOAc (3×200 ml) and the combined organic extracts were washed with water (3×200 ml) and allowed to stand over night. The resulting solid was collected by filtration and dried in vacuo to afford the title compound. The mother liquor was evaporated to give a yellow/brown oily solid which was triturated with ethanol (100 ml). The solid was collected by fitration, washed with EtOH and dried in vacuo to afford the title compound; [M+H]+ 390.

Aufarbeitung

  1. temperaturewith vigorous stirring, maintaining the reaction mixture at 45° C
  2. temperatureto cool to RT
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between EtOAc (600 ml) and water (2×200 ml)
  5. customThe aqueous portion was separated
  6. extractionextracted with EtOAc (3×200 ml)
  7. washthe combined organic extracts were washed with water (3×200 ml)
  8. waitto stand over night
  9. filtrationThe resulting solid was collected by filtration
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8d6acff6407349bdaa2d721c125b638b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115087B2

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