p-Toluenesulfonic acid → (NE)-4-chloro-N-(pyrimidin-5-ylmethylidene)benzenesulfonamide

反応式

[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([S:16](/[N:19]=[CH:1]/[C:3]2[CH:4]=[N:5][CH:6]=[N:7][CH:8]=2)(=[O:17])=[O:18])=[CH:14][CH:15]=1

参加物

実験手順

To a solution of 5-formyl pyrimidine (68, 1.0 g, 9.3 mmol) and 4-chlorobenzene sulfonamide (1.95 g, 10.2 mmol) in toluene (20 mL) was added 4 Å molecular sieves (1.0 g) and MP-TsOH (1.0 g). Dean-stark apparatus with reflux condenser was affixed to reaction vessel and reaction was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was taken up in EtOAc and filtered through Celite. The filtrate was concentrated in vacuo to yield 2.12 g (81%) 69 as a light brown solid, 1H NMR (CDCl3) δ 9.42 (s, 1H), 9.25 (s, 2H), 9.15 (s, 1H), 7.98 (d, 2H), 7.57 (d, 2H).