Thiourea → HCID 82049129, compound
Reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH3:13])=[CH:7][C:6]=1[CH3:14])=O.[NH2:15][C:16]([NH2:18])=[S:17]>CCO>[CH3:13][O:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]2[N:15]=[C:16]([NH2:18])[S:17][CH:2]=2)=[C:6]([CH3:14])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The mixture of 2-bromo-1-(4-methoxy-2,6-dimethylphenyl)ethanone (160 mg, 0.62 mmol) and thiourea (61 mg, 0.80 mmol) in EtOH (4 ml) was refluxed for 45 min. After that, all the solvent was removed in vacuo and to the residue was added H2O (50 ml). The resultant solution was extracted with CH2Cl2 (3×30 mL). The combined organic phases were dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo and the residue was purified by silica gel column (hexane/EtOAc=2/1 to 1/1) to afford 4-(4-methoxy-2,6-dimethylphenyl)thiazol-2-amine (132 mg, 90.9%) as light yellow solid. 1H NMR (500 MHz, CDCl3) δ 6.61 (s, 2H), 6.25 (s, 1H), 5.12 (br, 2H), 3.79 (s, 3H), 2.15 (s, 6H). 13C NMR (125.8 MHz, CDCl3) δ 166.7, 158.9, 149.8, 138.9, 127.9, 112.6, 105.9, 55.1, 20.6.