3-(3-Methylphenyl)-2-thioxo-1,3-thiazolidin-4-one

In the title compound, C10H9NOS2, the dihedral angle between the rhodanine (2-thioxo-1,3-thiazolidin-4-one) and 3-methylphenyl rings is 83.30 (3)°. The H atoms of the methyl group are disordered over two set of sites with an occupancy ratio of 0.58 (3):0.42 (3). In the crystal, the molecules interact by way of C—H⋯π and C=O⋯π interactions.

In the title compound, C 10 H 9 NOS 2 , the dihedral angle between the rhodanine (2-thioxo-1,3-thiazolidin-4-one) and 3-methylphenyl rings is 83.30 (3) . The H atoms of the methyl group are disordered over two set of sites with an occupancy ratio of 0.58 (3):0.42 (3). In the crystal, the molecules interact by way of C-HÁ Á Á and C OÁ Á Á interactions.
The purpose of synthesis of differet rhodanine derivatives is to study the biological activities. The title compound (I, Fig.   1) is being reported in this context.

Experimental
The title compound was prepared by a three step reaction procedure. In the first step meta toluidine aniline (10.7 g, 0.1 mol) and triethylamine (50.5 g, 0.5 mol) were stirred in ethanol (20 ml) followed by dropwise addition of CS 2 (15.2 g, 0.2 mol) while keeping the flask in an ice bath. The precipitate obtained were filtered off and washed with diethyl ether.
In second step, a solution of sodium chloroacetate (11.6 g, 0.1 mol) and chloroacetic acid (18.9 g, 0.2 mol) was prepared in 50 ml distilled water. To this solution the precipitates obtained in first step were added gradually and stirred at 273 K.
This mixture was stirred untill it turned light yellow.
In third step the yellow mixture was mixed in 140 ml hot (363-368 K) hydrochloric acid (6 N) and stirred for five minutes to obtain colorless crystalline precipitates. These precipitates were recrystalized in chloroform to get light yellow prisms of (I).
supplementary materials sup-2 Figures   Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. as those based on F, and R-factors based on ALL data will be even larger.