A Novel Heteroaromatic System: 2,1,3-Benzothiadiazinylium Derivatives

✍ Scribed by Dr. habil. Wolfgang Kosbahn; Dr. Helmut Schäfer

• Publisher: John Wiley and Sons
• Year: 1977
• Tongue: English
• Weight: 141 KB
• Volume: 16
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.197707801

✦ Synopsis

with stirring into ice-water and the crude product extracted into chloroform. The chloroform extract was passed through a short (100 x 15 mm) column of silica gel and the residue after removal of solvent was recrystallized from methanolwater to give (6d) as long silky needles (1.6g).

5-sec-Butyl-4,6-dichloro-2-phenylpyrimidine ( 6 b ) and 5-sec-But):l-6-chloro-3-methyI-2-phenyl-4-pyrirnidinone (7 b): ( I b )

(3.0 g, 0.02 mol) and (4a), (3.0 g, 0.02 mol) were reacted together in POC13 as described above for ( 6 d ) . Chromatography of the product on silica gel using chloroform-petroleum ether (b.p. 60--80°C) (1:l) as eluent gave ( 6 b ) as a pale yellow oil (2.9 g) which, after solidification, crystallized from ethanol in the form of colorless needles. Subsequent elution of the column with chloroform gave ( 7 b ) as a yellow oil (1.2 g), which solidified. Crystallization from a small quanity of petroleum ether (b.p. 60-80°C) gave colorless prisms.