[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[CH2:7][C:8]([S:10][C:5]=2[CH:4]=1)=[O:9].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([OH:23])[C:18](=[CH:21][CH:22]=1)[CH:19]=O>C(O)C.C(Cl)Cl.C(N(CC)CC)C>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]2[CH:19]3[S:10][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=4[CH:7]3[C:8](=[O:9])[O:23][C:17]=2[CH:16]=1To a stirred solution of 6-methoxythianaphthen-2-one (see Docket B-9459) (20 g, 111 mmol) in a mixture of ethanol (100 mL) and methylene chloride (50 mL) was added 4-methoxysalicylaldehyde (17.5 g, 115 mmol) followed by triethylamine (567 mg, 784 mL, 5.6 mmol) at room temperature. After 30 min, a solid began to precipitate and stirring was continued overnight. The mixture was then diluted with cold hexane (1 L) and filtered to yield 28.7 g (82%) of the title product as an off-white solid, pure by 1 H-NMR analysis. An analytical sample was obtained by recrystallization from toluene as light yellow crystals, mp 157-165 d°C.: 1 H-NMR (300 MHz, CDCl3) d 7.33 (d, J=8.6 Hz, 1H), 7.31 (d, J=8.1 Hz, 1H), 6.75 (d, J=2.4 Hz, 1H), 6.70 (m, 2H), 6.60 (d, J=2.5 Hz, 1H), 5.22 (d, J=7.2 Hz, 1H), 4.33 (d, J=7.2 Hz, 1H), 3.79 (s, 3H), 3.76 (s, 3H); IR (CHCl3) 1759 cm-1 ; MS (FD) m/e 314 (M+); Anal. calc'd. for C17H14O4S: C, 64.95; H, 4.50. Found: C, 65.01; H, 4.58.
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