Dicyclohexylcarbodiimide → 2-Pyrrolidinone, 1-((4-chlorophenyl)sulfonyl)-

HRID 1762457

Reaktionsgleichung

Reaktionsgleichung von HRID 1762457
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:12][CH2:13][CH2:14][C:15]2=[O:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 10868DicyclohexylcarbodiimideHCID 20534824-{[(4-Chlorophenyl)sulfonyl]amino}butanoic acid

Produkt 1

HCID 6675352-Pyrrolidinone, 1-((4-chlorophenyl)sulfonyl)-Ausbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In 20 ml of tetrahydrofuran was dissolved 2.78 g of N-(4'-chlorobenzenesulfonyl)-4-aminobutyric acid (0.01 mole). To the stirred solution on an ice bath was added 2.06 g of dicyclohexylcarbodiimide (0.01 mole), and the mixture was stirred at 0° C. for 21 hours. The reaction mixture was filtered, and the solid material was washed with anhydrous tetrahydrofuran. The filtrate and the washings were combined, and tetrahydrofuran was removed under reduced pressure. The residue thus obtained was recrystallized from a mixed solvent of chloroform-ether to give 2.37 g of N-(4'-chlorobenzenesulfonyl)-2-pyrrolidone as crystals. Physical properties were identical with those in Synthetic Example 3.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe solid material was washed with anhydrous tetrahydrofuran
  3. customtetrahydrofuran was removed under reduced pressure
  4. customThe residue thus obtained
  5. customwas recrystallized from a mixed solvent of chloroform-ether

Quellen und Nachweise

ORD-Eintrag
ord-4e17afe515de4ed6bdec791d6f3984de
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04833156

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