Sodium Glycolate → N-[6-(2-hydroxy-ethoxy)-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfon-amide

HRID 326708

Reaktionsgleichung

Reaktionsgleichung von HRID 326708
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.[C:27]([O-])(=[O:30])[CH2:28][OH:29].[Na+].[Na]>C(O)CO>[OH:29][CH2:28][CH2:27][O:30][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 517347Sodium GlycolateHCID 5360545SodiumHCID 19735459N-[6-chloro-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfonamide

Produkt 1

HCID 19735450N-[6-(2-hydroxy-ethoxy)-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfon-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

190 mg of N-[6-chloro-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfonamide were added to a sodium glycolate solution from 46 mg of sodium in 1 ml of ethylene glycol. After a reaction period of 5 hours at 100° C., the reaction mixture was evaporated to dryness under reduced pressure. The residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase was washed neutral, dried and evaporated under reduced pressure. The residue was chromatographed on silica gel with methylene chloride and ethyl acetate (4:1 v/v). There were obtained 175 mg of N-[6-(2-hydroxy-ethoxy)-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfon-amide, melting point 147°-149° C. (from methylene chloride/hexane).

Aufarbeitung

  1. customAfter a reaction period of 5 hours at 100° C.
  2. customthe reaction mixture was evaporated to dryness under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  4. washThe organic phase was washed neutral
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silica gel with methylene chloride and ethyl acetate (4:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-e2b486f0faba44978e09600883630e9b
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270313

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