4-Toluenesulfonyl chloride → HCID 13362030, Verbindung

HRID 980952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 980952
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]([CH2:14][OH:15])[CH:9]1[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:24](Cl)([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>[K]>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]([CH2:14][O:15][S:24]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:9]1[C:16]1[C:17]([Cl:23])=[CH:18][CH:19]=[CH:20][C:21]=1[Cl:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 13362029HCID 13362029, Verbindung

Produkt 1

HCID 13362030HCID 13362030, VerbindungAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5462222PotassiumLösungsmittel

Versuchsvorschrift

To 40 g of 1-benzyl-2-(2,6-dichlorophenyl)-3-hydroxymethyl-pyrrolidine-5-one in 67 ml of potassium dried pyridine at 5°-10° was added 23.3 g of tosyl chloride over 30 minutes. After the addition, the mixture was stirred for 3 hours at 15° and then for 13 hours at ambient temperature. The reaction mixture was added dropwise to a stirred ice-water solution and then set at ambient temperature for 72 hours. The light yellow solid was collected by filtration and then air dried. Trituration with ether followed by filtration provided 44.5 g of colorless crystals, m.p. 110°-114°.

Aufarbeitung

  1. additionAfter the addition
  2. waitfor 13 hours at ambient temperature
  3. waitset at ambient temperature for 72 hours
  4. filtrationThe light yellow solid was collected by filtration
  5. customair dried
  6. filtrationTrituration with ether followed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-cb0c90902d7449b08e0389612e35ca27
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04639529

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