Sodium Chloride → HCID 21901780, Verbindung

HRID 719738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 719738
S(Cl)(C)(=O)=O.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH2:17][CH:16]2[CH2:20]O)=[CH:11][CH:10]=1)([O-:8])=[O:7].C(N(CC)CC)C.[Cl-:29].[Na+]>CN(C=O)C>[Cl:29][CH2:20][CH:16]1[CH2:17][CH2:18][CH2:19][N:15]1[C:12]1[CH:13]=[CH:14][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6056432-Pyrrolidinemethanol, 1-(4-nitrophenyl)-

Produkt 1

HCID 21901780HCID 21901780, VerbindungAusbeute 882,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

27.9 ml (0.36 mol) of mesyl chloride were added dropwise to a solution of [1-(4-nitrophenyl)pyrrolidin-2-yl]methanol (66.7 g, 0.03 mol), 300 ml of anhydrous DMF and 58.5 ml (0.42 mol) of anhydrous triethylamine, cooled in an ice bath. The temperature was allowed to rise to 20° C. over one hour with stirring. 35.2 g (0.6 mol) of sodium chloride were added and the mixture was heated at 100° C. for one hour. The reaction medium was poured into 1.4 l of ice-water. The precipitate was filtered off, washed with water, dried and recrystallized from isopropanol. 63.7 g of a yellow powder (1) were thus obtained.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried
  5. customrecrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-db83a59d84f545d3a4a2b3b805ca0889
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132543B2

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