2-Benzothiazoleacetonitrile

A mixture of 2-aminothiophenol 3 (0.01 mol, 1.1 ml) and malononitrile (0.01 mol, 0.64 ml) in ethanol (10 ml) was stirred at 25° C for 5 h. The yellow solid was collected by filtration and recrystallized from ethanol to give light brown crystals; yield 86percent; mp 102 °C; A mixture of o-aminothiophenol (1) (0.01 mol) and malononitrile (0.01 mol) was stirred in absolute ethanol (10 ml) and glacial AcOH (1 ml) at RT for 10 h, the precipitate was filtered and crystallized from the proper solvent. 2: yellow powder (85percent); mp 100-102 °C (EtOH) refPreviewPlaceHolder[56] and refPreviewPlaceHolder[57].4.3.1 66.1 g (1 mol) of malononitrile, 600 ml of methanol, and 56 ml of acetic acid are mixed and stirred. 125 g (1 mol) of aminobenzenethiol is added dropwise thereto, and then the mixture is stirred for 10 hours at room temperature. After completion of the stirring, the mixture was filtered, washed with methanol, and dried. Thus, 134.6 g (77percent) of Intermediate 1 was obtained. [0347] Meanwhile, the data for To solution of 2-aminobenzenethiol (2.5 g, 19.97 mmol) in absolute ethanol (25 ml), malanonitrile (1.32 g, 19.97 mmol) was added, stirred and refluxed at 50 °C for 2 h along with catalytic amount of glacial acetic acid. To a solution of 2-aminobenzenethiol (10 g, 80 mmol) in ethanol (200 mL) was added propanedinitrile (16.65 g, 200 mmol), AcOH (200 mL) and the reaction was stirred overnight at RT. The resulting mixture was concentrated in vacuo and then diluted with HTo a solution of malonodinitrile (13.22 g, 0.200 mole) in dry chloroform(100 mL) was added ethanol (9.2 g, 0.200 mole). Hydrogen chloride (8.0 g, 0.220 mole) was passed into the solution at room temperature and the resulting suspension was stirred for an additional 16 hours at room temperature. The excess of hydrogen chloride was removed by passing dry nitrogen into the reaction mixture. A General procedure: Synthesis of benzothiazole derivatives(3 a-p) was carriedout according to the procedure reported by Kenny andMashelkar (2006). Different benzaldehydes (2, 5.5 mmol)and 2-aminothiophenol (1, 5 mmol) were taken in a roundbottomflask containing 7 ml of acetic acid. The reactionmixture was refluxed for 5–6 h (Scheme 1). The reactionwas monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature anddecomposed over ice–water mixture. The solid thusobtained was collected by filtration. The crude product waspurified either by crystallization using ethanol or by columnchromatography using hexane: ethyl acetate as solvent.All the synthesized compounds were characterized byspectroscopic methods.2-(Cyanomethyl)-1, 3-benzothiazole (3a) Compound 3awas obtained as yellowish powder in 75 percent yield, Mp98–100° C; IR (KBr) mmax: 3061, 2252, 1556, 1433, 1307 cm-1; 1H NMR (DMSO-d6, 400 MHz): δ = 8.2 (1H, d, J = 8.0 Hz, H-7), 8.1 (1H, d, J = 8.0, H-4), 7.55 (1H, t, J = 7.4 Hz, H-5), 7.45 (1H, t, J = 7.4 Hz, H-6), 4.88 (2H, s, CH2); 13C NMR (DMSO-d6, 100 MHz): δ = 160.4 (C, C-2), 152.2 (C, C-3a), 135.0 (C, C-7a), 126.4 (CH, C-7), 125.5 (CH, C-6), 122.5 (CH, C-5), 122.2 (CH, C-4), 116.4(CN, C-20), 22.3 (CH2, C-10); EIMS: m/z 174 [M+]; Anal.Calcd for C9H6N2S: C, 62.04; H, 3.47; N, 16.07 Found: C, 62.11; H, 3.39, N, 16.13.

Molecular Weight:174.22
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:174.02516937
Monoisotopic Mass:174.02516937
Topological Polar Surface Area:64.9
Heavy Atom Count:12
Complexity:208
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes