Methanol → Cyclosulfamuron
Reaktionsgleichung
[CH3:1][O-:2].[Na+].[CH:4]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:16]([NH:19][C:20]([NH:22][C:23]2[N:28]=[C:27](Cl)[CH:26]=[C:25](Cl)[N:24]=2)=[O:21])(=[O:18])=[O:17])=[O:8])[CH2:6][CH2:5]1.[CH3:31][OH:32]>>[CH:4]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:16]([NH:19][C:20]([NH:22][C:23]2[N:28]=[C:27]([O:2][CH3:1])[CH:26]=[C:25]([O:32][CH3:31])[N:24]=2)=[O:21])(=[O:18])=[O:17])=[O:8])[CH2:6][CH2:5]1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A mixture of sodium methoxide (1.08 g, 0.02 mol) in methanol is added slowly to a mixture of 1-{[o-(cyclopropyl)phenyl]sulfamoyl}-3-(4,6-dichloro-2-pyrimidinyl)urea from Example 1 (4.30 g, 0.01 mol) in methanol at 60° C. The reaction mixture is heated at 60° C. for two hours, cooled, treated with additional sodium methoxide (0.54 g), refluxed overnight, cooled, acidified and concentrated in vacuo to obtain a residue. The residue is slurried in methanol, filtered, washed sequentially with methanol and water, and dried in a vacuum oven at 55°-60° C. to give the title product as a cream colored solid (2.2 g, 98.6% real by HPLC analysis, 70% yield, mp 168.5°-169.5° C.).