6,7-dichloro-2,3-dihydro-1H-inden-1-one

5 (Compound 153) Thionyl chloride (5.73 mL, -79 mmol) and 2, 3-dichloro-benzoic acid (commercially available from Aldrich) (10.0 g, 52.4 mmol) in benzene was heated to reflux until no more gas evolution was observed. After cooling to rt the mixture was concentrated. The concentrate was diluted with dichloroethane and added to A1C13 (7.0 [G, ~53 MMOL)] in dichloroethane at [10-20 °C.] Ethylene was bubbled through the mixture for 4 h. The mixture was stirred overnight and quenched with 4 N [HCI.] The resulting layers were separated and the aqueous layer was extracted with Et2O (3 x 250 mL). The combined organic extracts were washed with H2O (3 x 150 mL), saturated [NAHC03] (3 x 150 mL), brine [(1] x 150 mL), dried over [MGS04] and concentrated. The concentrate was added to a slurry [OF ALCL3] (9.0 g) and NaCl (2.4 g) at [130 °C.] The resulting mixture was stirred at [180 °C] for 2 hours after which it was cooled to room temperature and quenched with ice followed by concentrated [HC1.] The mixture was extracted with [CH2CL2] (3 x 500 mL) and the combined organic extracts were concentrated and purified by column chromatography using 20percent EtOAc: hexane eluant to give 6.8 g (80percent) [OF 6, 7-DICHLORO-1-INDANONE.] Use of 6, 7- [DICHLORO-INDAN-1-ONE] in Method NINETEEN produced [4- (4, ] 5-dichloro-indan-2-yl) - [1, ] 3-dihydro-imidazole-2-thione (Compound 153). 1H NMR (300 MHz, [MEOH-D4)] [6] 7.31 (d, J= 7.8 Hz, [1H), ] 7.14 (d, J= 8.1 Hz, [1H), ] 6.62 (s, 1H), 3.67-3. 56 [(M, ] 1H), 3.42-3. 31 [(M, ] 2H), 3.09-2. 99 [(M, ] 2H).Example NINETEEN-5

Molecular Weight:201.05
XLogP3:2.9
Hydrogen Bond Acceptor Count:1
Exact Mass:199.9795702
Monoisotopic Mass:199.9795702
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:205
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes