2-Amino-5-(4-chlorophenyl)thiazole synthesis
- Product Name:2-Amino-5-(4-chlorophenyl)thiazole
- CAS Number:73040-66-1
- Molecular formula:C9H7ClN2S
- Molecular Weight:210.68
99-91-2
17356-08-0
73040-66-1
According to the method reported by Siddiqui et al [17], p-chloroacetophenone (0.01 mol) and thiourea (1.52 g, 0.02 mol) were used as raw materials and iodine (2.54 g, 0.01 mol) was added for the reaction. The reaction mixture was heated in an oil bath at 100 °C overnight. After completion of the reaction, it was cooled to room temperature and the reaction mixture was washed with diethyl ether (100 mL) to remove unreacted iodine and p-chloroacetophenone. The solid residue was dissolved in cold water (200 mL) and the pH was adjusted to 9-10 with 25% aqueous ammonium hydroxide.The precipitated 2-amino-5-(4-chlorophenyl)thiazole was collected by filtration and purified by recrystallization with hot ethanol. The product 2-amino-5-(4-chlorophenyl)thiazole (1) had a yield of 81% and a melting point of 168-170 °C. FTIR (KBr pressed sheet, cm?1 ): 3439, 3284 (NH?symmetric and asymmetric stretching vibrations), 1633 (C=N stretching vibration).1H NMR (DMSO-d?, 300 MHz, δ): 7.81-7.79 (d, 2H, benzene ring hydrogen), 7.41-7.38 (d, 2H, benzene ring hydrogen), 7.12 (s, 2H, NH?), 7.04 (s, 1H, thiazole ring hydrogen). Elemental analysis (calculated values, C?H?ClN?S, 210.5 g/mol): C, 51.31; H, 3.33; N, 13.30; S, 15.20. measured values: C, 51.55; H, 3.39; N, 13.50; S, 15.33.
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Yield:73040-66-1 81%
Reaction Conditions:
with iodine at 100;
Steps:
General procedure for preparation the compounds 1-3
General procedure: These compounds were prepared according to the procedurethat was described in Siddiqui et al.[17] The title compoundswere prepared by the addition of iodine (2.54 g,0.01 mol) to the 4-substituted acetophenone (0.01 mol) andthiourea (1.52 g, 0.02 mol), followed by heating of the mixtureovernight in an oil bath at 100C. After cooling, thereaction mixture was washed with diethylether (100 mL) toremove any unreacted iodine and substituted acetophenone.The solid residue was put in (200 mL) of cold water andtreated with 25% aqueous ammonium hydroxide (to pH 9-10). The precipitated thiazoles were collected and purifiedby crystallization from hot ethanol. 2-Amino-4-(4-chlorophenyl)-thiazole (1): Yield (81%);mp: 168-170C; FTIR (KBr disk cm1): 3439, 3284 symm.and asymm. NH2 group, 1633 (C D N); 1H NMR (DMSOd6,300 MHz, d): 7.81-7.79 (d, 2H, phenyl), 7.41-7.38 (d,2H, phenyl), 7.12 (s, 2H, NH2), 7.04 (s, 1H, thiazole ring);Anal. Calcd. for C9H7ClN2S (210.5 g/mol): C, 51.31; H,3.33; N, 13.30; S, 15.20. Found: C, 51.55; H, 3.39; N, 13.50;S, 15.33.
References:
Tomi, Ivan Hameed R.;Al-Daraji, Ali H. R.;Aziz, Sherien A. [Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2015,vol. 45,# 4,p. 605 - 613]
