4-(2-Bromo-acetyl)-benzoicacid

General procedure: 1 mmol of the required acetophenone was dissolved in 10 mL of AcOH. Then 1 equiv. of bromine was dissolved in 10 mL of AcOH and then added drop wise to the reaction mixture. Then the reaction was stirred at room temperature for 4 h. The solvent was evaporated to dryness and the product was purified using normal phase column chromatography with gradient increase of methanol in dichloromethane as eluent.To a stirred mixture of thiocarbonyidiimidazole (44.9 mmol) in THF (40 mL) at room temperature was added portionwise 2 M Dimethylamine in THF (44 mmol) and a temperature increase was observed. 40 min after final addition the reaction mixture was heated to 55 °C for 1 h, then allowed to reach room temperature again. The reaction was then concentrated in vacuo and the residue purified by flash chromatography (silica gel, Petroleum ether-EtOAc) to give the intermediate Imidazole-1-carbothioic acid dimethylamide. This material was treated with freshly prepared sat. ammonia in methanol (40 mi) for 60 h, then concentrated in vacuo and the precipitated residue was suspended in diethyl ether and collected by filtration. The precipitate was washed with diethyl ether and air-dried to give a slight yellow solid (1.71 g, 16.4 mmol) which was used in the subsequent step. 4- (2-bromoacetyl) benzoic acid (1.23 mmol) and 1- piperidinethiocarboxamide (1. 23 mmol) were mixed in THF (10 mL), then refluxed for 3 h. The reaction mixture was then allowed to reach room temperature and the obtained precipitate was collected by filtration and washed with 3 portions of diethyl ether. The crude product was crystallized from hot 1: 1 EtOH-EtOAc to give a first harvest of colorless needles (0.1 g, 0.40 mmol). 1H NMR (DMSO-d6, 400 MHz) 8 7.94 (4H, m), 7.37 (1H, s), 3.11 (6H, m).To a stirred mixture of thiocarbonyldiimidazole (44.9 mmol) in THF (40 ml_) at room temperature was added portionwise 2 M Dimethylamine in THF (44 mmol) and a temperature increase was observed. 40 min after final addition the reaction mixture was heated to 55 0C for 1 h, then allowed to reach room temperature again. The reaction EPO To thiocarbonyldiimidazole (2 g, 11.5 mmol) in THF (30 mL) at RT was added N- methylpiperazine (1.00 g, 10 mmol) drop wise. The reaction was stirred at RT for 2 h and then at 55 °C for 1 h. The reaction was cooled to RT and 20 mL of THF was removed in vacuo. 2M NH3 (10 mL) in MeOH was added and the reaction stirred for 15 h. A further 2M NH3 (10 mL) in MeOH was added and the reaction maintained at 55 °C for 8 h. A pale yellow precipitate (1.00 g) was observed and filtered off, dried and used directly in the next step. The thiourea (0.84 g, 5.2 mmol) was dissolved in EtOH (30 mL) and 4- (2-bromo-acetyl)-benzoic acid (1.28 g, 5.2 mmol) was added. The reaction was heated at reflux for 3 h. The reaction was cooled to RT and the solid filtered off. The solid was washed with Et20 and dried thoroughly. This procedure provided the title compound as a pale yellow solid (1.23 g, 77 percent).To thiocarbonyldiimidazole (2 g, 11.5 mmol) in THF (30 ml_) at RT was added N- methylpiperazine (1.00 g, 10 mmol) drop wise. The reaction was stirred at RT for 2 h and then at 55 'C for 1 h. The reaction was cooled to RT and 20 ml_ of THF was removed in vacuo. 2M NH3 (10 ml_) in MeOH was added and the reaction stirred for 15 h. A further 2M NH3 (10 ml_) in MeOH was added and the reaction maintained at 55 'C for 8 h. A pale yellow precipitate (1.00 g) was observed and filterered off, dried and used directly in the next step. The thiourea (0.84 g, 5.2 mmol) was dissolved in EtOH (30 ml_) and

A phenacyl bromide

Molecular Weight:243.05
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:241.95786
Monoisotopic Mass:241.95786
Topological Polar Surface Area:54.4
Heavy Atom Count:13
Complexity:207
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes