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Water → 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide

HRID 1358318
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1358318
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.[K+].[C:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH-:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].O>CS(C)=O>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:30][C:2]2[C:7]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=2)(=[O:28])=[O:29])=[CH:23][CH:22]=1)([CH3:20])([CH3:18])[CH3:19]
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Komponenten

5

Edukt 3

HCID 962WaterHCID 219795544,6-Dichloro-5-(4-methylphenyl)pyrimidineHCID 131721323HCID 131721323, Verbindung

Produkt 1

HCID 227294154-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamideAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 0.8 g of 4,6-dichloro-5-(p-tolyl)-pyrimidine and 1.68 g of 4-tert.-butylbenzene sulfonamide potassium salt in 20 ml of DMSO was stirred at room temperature for 24 h. The mixture was poured onto 200 ml of water and extracted twice with 100 ml of diethyl ether. The organic layers was extracted twice with 50 ml of water. The combined aqueous layers was acidified with conc. hydrochloric acid. The resulting fine suspension was extracted twice with ethyl acetate. The combined organic layers was dried over Na2SO4 and evaporated. The residue was dried under high vacuum to give 1.34 g 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-benzene sulfonamide as a white powder. LC-MS: tR=5.92 min, [M+1]+=416.20, [M−1]−=414.24.

Aufarbeitung

  1. extractionextracted twice with 100 ml of diethyl ether
  2. extractionThe organic layers was extracted twice with 50 ml of water
  3. extractionThe resulting fine suspension was extracted twice with ethyl acetate
  4. dry with materialThe combined organic layers was dried over Na2SO4
  5. customevaporated
  6. customThe residue was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-494b30d6a5b24b96846952907ba0baac
Quelldatensatz
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06596719B1

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