Water → p-t-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide

HRID 1358324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358324
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[CH:4][N:3]=1.[K+].[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH-:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].O>CS(C)=O>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[CH:4][N:3]=2)(=[O:30])=[O:31])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Komponenten

5

Edukt 3

HCID 962WaterHCID 15819130HCID 15819130, VerbindungHCID 131721323HCID 131721323, Verbindung

Produkt 1

HCID 15819129p-t-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 2 g of 4,6-dichloro-5-(o-methoxyphenoxy)-pyrimidine in 40 ml of DMSO 3.7 g of 4-tert.-butylbenzene sulfonamide potassium salt was added. The resulting solution was stirred for 20 h at room temperature. Eventually, the mixture was poured onto 400 ml of water and washed twice with 200 ml of diethyl ether. The organic layers was extracted with 200 ml of water. The combinded aqueous layers was acidified with conc. hydrochloric acid. The mixture was cooled to 0° C. and 100 ml of brine was added. The precipitate that formed was collected and dried to yield 2.7 g of 4-tert.-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-4-pyrimidinyl]-benzene sulfonamide as a white powder. LC-MS: tR=5.80 min, [M+1]+=448.17, [M−1]−=446.21.

Aufarbeitung

  1. washwashed twice with 200 ml of diethyl ether
  2. extractionThe organic layers was extracted with 200 ml of water
  3. temperatureThe mixture was cooled to 0° C.
  4. addition100 ml of brine was added
  5. customThe precipitate that formed
  6. customwas collected
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9ef520da38ab408da4620f6240fa126c
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596719B1

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