4,5,6,7-Tetrahydro-2-benzothiazolamine

General procedure: A mixture of the acetophenone (2 mmol), thiourea (3 mmol) and iodine (2 mmol), in the presence of 0.03 g nanochitosan was refluxed in EtOH. 1.52 g (20 mmol) of thiourea and 2538 mg (10 mmol) of iodine were added to 1.04 ml (10 mmol) of cyclohexanone and the mixture was stirred at 100 ° C for 6 hours. After 6 hours, hot water was added to the residue and the mixture was further stirred for 30 minutes. The residue was neutralized with NaHCO3 (aq) and extracted with diethyl ether. The extracted organic layer was washed with brine Washed with brine and dried over anhydrous MgSO4. The filtrate was concentrated under reduced pressure, and the obtained residue was subjected to column chromatography (EtOAconly) to obtain Compound 1 (1.23 g, 80percent).A mixture of cyclohexanone (3.9g, 39.8mmol), dissolved in 20ml of dry toluene, was added with stirring thiourea (6.1g, 80.3mmol) was a suspension, was added iodine (10.2g, 40.2mmol), plus complete heating 100 the reaction, 48h after distilling off the solvent under reduced pressure, the resulting solid was dissolved in 150ml of hot water, then cooled to 0 deg.] C, large amount of solid precipitated.After filtration and washing the filter cake was dissolved in 100ml hot water drops to room temperature and filtered, the filtrate was adjusted to alkaline pH with aqueous ammonia, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated to give after column chromatography 3.49 pale yellow needle crystal g, yield 57percentGeneral procedure: A mixture of ketone (11a or 11b) (10.0 mmol, 1.0 equiv), thiourea(20.0 mmol, 2.0 equiv) and iodine (10.0 mmol, 1.0 equiv)was stirredin sealed tube at 110 C for 12 h. The reaction mixturewas cooled toroom temperature. Then hot water (10 mL) was added to solubilizethe crude material, and the resulting solutionwas stirred for further30 min. The mixture was allowed to cool to room temperature, andthe water layer was washed with diethyl ether. The aqueous layerwas separated and was neutralized by the careful addition of solidsodium bicarbonate. The aqueous layer was extracted with trichloromethane.And the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuum.The resulting residue was purified by silica gel chromatography(dichloromethane/methanol 1percent aqueous ammonia, v/v, 99:1 to98:2) to give the desired product.A mixture of cyclohexanone (3.0 g, 30.6 mmol), thiourea (4.65 g, 61.1 mmol) and iodine (7.76 g, 30.6 mmol) was stirred at 110 °C for 12 h. The reaction mixture was cooled to room temperature. Hot water was then added and the resulting solution was stirred for 30 min. The aqueous solution was washed with diethyl ether and then neutralized by the addition of solid NaHCO30 mg (0.19 mmol) of 4, 5, 6, 7-tetrahydrobenzo [d] thiazol-2-amine 53 mg (0.19 mmol) of 2, 4'-dibromoacetophenone was dissolved in 3 ml of ethanol and stirred in a microwave reactor at 150 C for 20 minutes. The residue was concentrated under reduced pressure and subjected to column chromatography (EtOAc: Hex = 1: 5) to obtain Compound 2c (14 mg, 22%).(4, 5, 6, 7-Tetrahydrobenzo [d] thiazol-2-amine, 46.2 mg, 0.3 mmol) and 2-bromo- 4'-fluoroacetophenone (70 mg, 0.3 mmol) was dissolved in ethanol (3 ml) and stirred in a microwave reactor at 150 C for 20 minutes. The residue was concentrated under reduced pressure and subjected to column chromatography (EtOAc: Hex = 1: 5) to obtain Compound 2b (18.9 mg, 22%).4, 5, 6, 7-tetrahydrobenzo [d] thiazol-2-amine and 64 mg (0.3 mmol) of 2-bromo-4'-methylacetophenone were dissolved in 3 ml of ethanol and stirred in a microwave reactor at 150 C for 20 minutes. The residue was concentrated under reduced pressure and subjected to column chromatography (EtOAc: Hex = 1: 4) to obtain 2 g (22.3 mg, 28%) of the compound.

Molecular Weight:154.24
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:154.05646950
Monoisotopic Mass:154.05646950
Topological Polar Surface Area:67.2
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes