2,3-Diphenyl-1,3-thiazolidin-4-one

Abstract

Key indicators: single-crystal X-ray study; T = 298 K; mean (C-C) = 0.003 Å; R factor = 0.049; wR factor = 0.147; data-to-parameter ratio = 19.5.The title compound, C 15 H 13 NOS, is a chiral molecule crystallized as a racemate, with two molecules in the asymmetric unit. In each of the molecules, the five-membered thiazine ring has an envelope conformation, with the S atom forming the flap. In one molecule, the angle between the two phenyl-ring planes is 82.77 (7) , while in the other it is 89.12 (6) . In the crystal, molecules are linked into chains along the b-axis direction by C-HÁ Á ÁO hydrogen bonds. Related literature

T3P‐promoted synthesis of a series of novel 3‐aryl‐2‐phenyl‐2,3‐dihydro‐4H‐1,3‐benzothiazin‐4‐ones

“…The low yields in general are a function of the two substrates. We have seen that reactions using 3‐mercaptopropionic acid are much faster and higher yielding than thiosalicylic acid, presumably because the aromatic thiol is less nucleophilic. As discussed earlier, the N ‐aryl group on the imine makes the reaction slower and lower yielding than an N ‐alkyl.…”

Synthesis and Spectroscopic Properties of 2,3-Diphenyl-1,3-thiaza-4-one Heterocycles

“…The crude product was further purified as indicated in previous reports or as below. X-Ray structures, melting points, and TLC retention factors have also been previously reported (Yennawar & Silverberg, 2013, Yennawar, Bendinsky et al, 2014, Yennawar, Singh & Silverberg, 2014, Yennawar, Tierney & Silverberg, 2014, Yennawar, Singh & Silverberg, 2015. 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one (6): The reaction was repeated after the original report (Yennawar, Bendinsky et al, 2014).…”

“…After chromatography, slow recrystallization from ethanol gave slightly yellow crystals (0.6676 g, 35.1% yield), m.p. 8, 142.5, 139.5, 133.3, 132.4, 130.4, 129.5, 129.2, 128.5, 128,3, 127.7, 127.2, 126.6, 126.4, 125.9, 65.3 2,3,5,-one (4) (Yennawar, Tierney & Silverberg, 2014 169.7, 142.7, 139.7, 129.2, 128.6, 128.1, 127.3, 126.8, 126.7, 65.8, 34.5, 22.7 2, 1592.0, 1494.3, 1415.7, 1393.3, 1330.6, 1278.5, 1218.1, 1194.3, 774.3, 739.6, 720.4, 708.8, 690.3. UV/Vis:  max : 272 nm (methanol).…”

rac-cis-5-Methyl-2,3-diphenyl-1,3-thiazolidin-4-one

“…Woolston et al (1993) have reported observing a 3:1 cis:trans ratio in the product, although the method of isolation was not specified. We have previously reported the structure of 2,3-diphenyl-1,3-thiazolidin-4-one (Yennawar et al, 2014). The most closely related 5-methyl compound whose crystal structure is known is data reports the 3-(p-chlorophenyl)-2-(8-quinolinyl) compound of Ö zturk et al (2000), which displayed an envelope conformation for the thiazolidinone ring.…”