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Sodium Hydroxide → 3-[(4-Chlorophenyl)sulfonyl]-1-(phenylmethyl)pyrrolidine maleate

HRID 236081
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 236081
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH:17]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18]2)=[CH:12][CH:11]=1.B(O[O-])=[O:30].[Na+].[OH-:34].[Na+]>S(=O)(=O)(O)O>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([CH:17]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:18]2)(=[O:30])=[O:34])=[CH:14][CH:15]=1
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Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 517072Sodium PerborateHCID 704459303-[(4-Chlorophenyl)thio]-1-(phenylmethyl)pyrrolidine maleate

Produkt 1

HCID 704459533-[(4-Chlorophenyl)sulfonyl]-1-(phenylmethyl)pyrrolidine maleate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A mixture of 12.88 g (0.0425 mole) of 3-[(4-chlorophenyl)thio]-1-(phenylmethyl)pyrrolidine maleate and 27 g (0.175 mole) of sodium perborate in 500 ml of 2M sulfuric acid was refluxed for 17 hr. The reaction mixture was poured over ice and the solution made basic with 50% sodium hydroxide solution. The resulting solution was extracted with several portions of methylene chloride. The methylene chloride phase was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil, the free base of the title compound. The maleate salt was prepared and recrystallized from methanol-diethyl ether as in Preparation 2 to give 13.77 g (70.6%) of the product as a white crystalline solid, m.p. 154.5°-155° C.

Aufarbeitung

  1. temperaturewas refluxed for 17 hr
  2. additionThe reaction mixture was poured over ice
  3. extractionThe resulting solution was extracted with several portions of methylene chloride
  4. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-c34c49dddceb44afa583cbc8dcb78631
Quelldatensatz
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04642348

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