p-Toluenesulfonic acid → HCID 59342358, Verbindung

HRID 15730

Reaktionsgleichung

Reaktionsgleichung von HRID 15730
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([S:16](/[N:19]=[CH:1]/[C:3]2[CH:4]=[N:5][CH:6]=[N:7][CH:8]=2)(=[O:17])=[O:18])=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 668244-ChlorobenzenesulfonamideHCID 2761034Pyrimidine-5-carboxaldehyde

Produkt 1

HCID 59342358HCID 59342358, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 5-formyl pyrimidine (68, 1.0 g, 9.3 mmol) and 4-chlorobenzene sulfonamide (1.95 g, 10.2 mmol) in toluene (20 mL) was added 4 Å molecular sieves (1.0 g) and MP-TsOH (1.0 g). Dean-stark apparatus with reflux condenser was affixed to reaction vessel and reaction was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was taken up in EtOAc and filtered through Celite. The filtrate was concentrated in vacuo to yield 2.12 g (81%) 69 as a light brown solid, 1H NMR (CDCl3) δ 9.42 (s, 1H), 9.25 (s, 2H), 9.15 (s, 1H), 7.98 (d, 2H), 7.57 (d, 2H).

Aufarbeitung

  1. temperatureDean-stark apparatus with reflux condenser
  2. customwas affixed to reaction vessel and reaction
  3. temperaturewas heated
  4. temperatureat reflux for 18 hours
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered through Celite
  7. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ee9130598be74c03a5d2ba3e8c103572
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732609B2

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