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Triethylamine → 8-{2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethylsulfonylamino}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran methanesulfonate

HRID 1452336
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1452336
ClC[CH2:3][S:4](Cl)(=[O:6])=[O:5].[NH2:8][C:9]1[C:18]2[O:17][C:16](C3C=CC=CC=3)=C(C)C(=O)[C:13]=2[CH:12]=[CH:11][CH:10]=1.[CH:27]([S:29]([NH:32][C:33]1[C:42]2[O:41][C:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[C:39]([CH3:49])[C:38](=[O:50])[C:37]=2[CH:36]=[CH:35][CH:34]=1)(=[O:31])=[O:30])=[CH2:28].[CH2:51]([N:53](CC)[CH2:54][CH3:55])[CH3:52]>>[CH3:3][S:4]([OH:6])(=[O:17])=[O:5].[CH3:16][O:17][C:18]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:8]1[CH2:55][CH2:54][N:53]([CH2:28][CH2:27][S:29]([NH:32][C:33]2[C:42]3[O:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[C:39]([CH3:49])[C:38](=[O:50])[C:37]=3[CH:36]=[CH:35][CH:34]=2)(=[O:31])=[O:30])[CH2:51][CH2:52]1
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Komponenten

5

Edukt 4

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 199728088-amino-3-methyl-4-oxo-2-phenyl-4H-1-benzopyranHCID 199728168-(ethenylsulfonylamino)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

Produkt 1

HCID 199725388-{2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethylsulfonylamino}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran methanesulfonate

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.05 ml of 2-chloroethanesulfonyl chloride was added dropwise to a solution of 5 g of 8-amino-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran and 1.4 ml of triethylamine stirred at 0° C. The reaction mixture was stirred at room temperature for 2 days. After filtering the precipitated solid, the solution was evaporated to dryness in vacuo to give a crude residue containing 8-(ethenYlsulfonylamino)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran used without further purification. A mixture of 7.54 g of this residue and 5.8 g of 1-(2-methoxyphenyl)piperazine and 4.15 g of potassium carbonate in 100 ml of dimethylformamide was stirred at room temperature for 4 hours, poured into 600 ml of water and extracted with ethyl acetate. The organic layer was evaporated to dryness in vacuo and the residue was purified-by column chromatography on silica gel eluting with petroleum ether-acetone 8:2. The collected fractions were evaporated to dryness in vacuo and crystallized from 70% ethanol to give 0.75 g of the title compound as a base. This solid was dissolved in dichloromethane and 1 equivalent of methanesulfonic acid was added to the solution. The crude methanesulfonate, obtained by evaporation in vacuo, was crystallized from acetone, yielding 0.6 g of the title compound melting at 202°-203° C.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 2 days
  2. filtrationAfter filtering the precipitated solid
  3. customthe solution was evaporated to dryness in vacuo
  4. customto give a crude residue
  5. customused without further purification
  6. additionA mixture of 7.54 g of this residue and 5.8 g of 1-(2-methoxyphenyl)piperazine and 4.15 g of potassium carbonate in 100 ml of dimethylformamide
  7. stirringwas stirred at room temperature for 4 hours
  8. additionpoured into 600 ml of water
  9. extractionextracted with ethyl acetate
  10. customThe organic layer was evaporated to dryness in vacuo
  11. customThe collected fractions were evaporated to dryness in vacuo
  12. customcrystallized from 70% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a04702363fad4cbcbf671983db57ee28
Quelldatensatz
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05605896

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