Pyridine → N-(2,2-Dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamide

HRID 1022864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022864
[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.N1C=CC=CC=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][N:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1)[S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)(=[O:30])=[O:29]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 11615438N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine

Produkt 1

HCID 59818264N-(2,2-Dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamideAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

20 g (2,2-Dimethoxy-ethyl)-(4-fluoro-benzyl)-amine (21) were dissolved in 120 ml of dichloromethane. 20 mL of pyridine are added. At 0° C. a solution of 23.8 g p-toluenesulfonic acid chloride in dichloromethane was added dropwise. The reaction was allowed to warm to room temperature and stirring is continued until conversion was completed. For workup, the reaction mixture was extracted twice with 2M hydrochloric acid, twice with sodium bicarbonate and once with brine. The organic layer was dried over magnesium sulfate, evaporated to dryness and the obtained crude product was purified by silica gel chromatography to yield 22.95 g of compound 22 as an orange oil. Rt=1.71 min (Method #4). Detected mass: 336.1 (M-OMe−).

Aufarbeitung

  1. extractionFor workup, the reaction mixture was extracted twice with 2M hydrochloric acid, twice with sodium bicarbonate and once with brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated to dryness
  4. customthe obtained crude product
  5. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-88a8ee16f4b944efaa6a556bb7aac318
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722671B2

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