Reaktion #1052805

Reaktionsgleichung

sodium

2-phenyl-ethenesulfonic acid(6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide

1,2-dimethoxyethan

ethyleneglycol

sodium

→

2-phenyl-ethenesulfonic acid[6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONwas completely dissolved
2. 2
   workup.ADDITIONwas added
3. 3
   SonstigeThe mixture was evaporated
4. 4
   workup.ADDITIONwater (150 ml) was added to the residue
5. 5
   workup.ADDITIONfollowed by addition of acetic acid (1.0 ml)
6. 6
   FiltrationThe precipitate was filtered off
7. 7
   Waschenwashed with water
8. 8
   Sonstigedried
9. 9
   SonstigeThe crude material was purified by chromatography over silicagel with EtOAc/methanol/aqueous ammonia (25%)=4/1/0.5

Vorschrift

To a mixture of 1,2-dimethoxyethan (15 ml) and ethyleneglycol (40 ml) was added sodium (298 mg) in small portions. The mixture was stirred until the sodium was completely dissolved. Then DMF (15 ml), followed by 2-phenyl-ethenesulfonic acid(6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (1.0 g) was added. Stirring was continued for 4 days at 100° C. The mixture was evaporated and water (150 ml) was added to the residue followed by addition of acetic acid (1.0 ml). The precipitate was filtered off, washed with water and dried. The crude material was purified by chromatography over silicagel with EtOAc/methanol/aqueous ammonia (25%)=4/1/0.5 to give 2-phenyl-ethenesulfonic acid[6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (500 mg). tR=4.54 (LC); M+=412.38 (ES+).

Quelle