Diethyl Ether → 2-Phenyl-ethenesulfonic acid [6-chloro-5-p-tolyl-pyrimidin-4-yl]-amide

HRID 965624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965624
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[K+].[C:26]1([CH:32]=[CH:33][S:34]([NH-:37])(=[O:36])=[O:35])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OCC)C>CS(C)=O>[Cl:15][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:37][S:34]([CH:33]=[CH:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:35])=[O:36])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 219795544,6-Dichloro-5-(4-methylphenyl)pyrimidineHCID 74047229HCID 74047229, Verbindung

Produkt 1

HCID 738818642-Phenyl-ethenesulfonic acid [6-chloro-5-p-tolyl-pyrimidin-4-yl]-amideAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To 4,6-dichloro-5-p-tolyl-pyrimidine (2.0 g) disolved in DMSO (35 ml) was added di-isopropyl-ethyl-amine (1.46 ml) followed by 2-phenyl-ethenesulfonamide potassium salt (2.78 g). The mixture was stirred for 48 h at rt then poured onto water (500 ml) and diethylether (250 ml) was added and the solution was stirred for 30 minutes. The layers were separated and the water layer was acidified with acetic acid (2.0 ml) and cooled to 0° C. for 1 h. The precipitated product was filtered off and washed with water and diethylether and dried to give 2-phenyl-ethenesulfonic acid(6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (2.02 g). tR=5.32 (LC); M+=386.23 (ES+); M−=384.22 (ES−).

Aufarbeitung

  1. additionwas added
  2. stirringthe solution was stirred for 30 minutes
  3. customThe layers were separated
  4. temperaturecooled to 0° C. for 1 h
  5. filtrationThe precipitated product was filtered off
  6. washwashed with water and diethylether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4194ace59e03460db986da8a14bb8414
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951856B2

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