3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride

2.86 kg of methylhydroxyethylthiazole, 8.58 kg of acetonitrile and 2.54 kg of benzyl chloride were charged in a 20 L reactor equipped with a stirrer and refluxed for 6.5 hours. After cooling the reaction solution to room temperature to give a solid, 3 kg of acetonitrile was added to the reaction solution and filtration was carried out. The obtained solid was washed with 2.0 kg of acetonitrile and dried under reduced pressure to obtain 2.36 kg of 3-benzyl-5- (2-hydroxyethyl) -4-methylthiazolium chloride (yield: 44percent ).Representative compounds of the present invention are:...3-(2-phenyl-2-oxoethyl)-4-methyl-5-(2-hydroxyethyl)thiazolium bromide;3-[2-(4-bromophenyl)-2-oxoethyl]-4-methyl-5-(2-hydroxyethyl)thiazolium bromide;3, 4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide;3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide;3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride;3-(2-methoxy-2-oxoethyl)benzothiazolium bromide;3-(2-phenyl-2-oxoethyl)benzothiazolium bromide;3-[2-(4'-bromophenyl)-2-oxoethyl]benzothiazolium bromide;...(19) 3-benzyl-5-(2-hydroxyethyl)-4-methyl thiazolium chloride, m.p. 144°-146° C.3-benzyl-5-(2-hydroxyethyl)-4-methyl thiazolium chloride, m.p. 144°-146° C.730 3-benzyl-5-(2-hydroxyethyl)-4-methyl thiazolium chloride, m.p. 144-146° C.Representative, non-limiting examples of compounds of the present invention are:...3-(2-phenyl-2-oxoethyl)-4-methyl-5-(2-hydroxyethyl)thiazolium bromide;3-[2-(4-bromophenyl)-2-oxoethyl]-4-methyl-5-(2-hydroxyethyl)thiazolium bromide;3, 4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide;3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide;3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride;3-(2-methoxy-2-oxoethyl)benzothiazolium bromide;3-(2-phenyl-2-oxoethyl)benzothiazolium bromide;3-[2-(4'-bromophenyl)-2-oxoethyl]benzothiazolium bromide;...(b) Preparation of the catalyst Synthesis of ethyl 2-acetyl-3-(3-bromo-5-fluorophenyl)-4-(4-chlorophenyl)-4-oxobutanoate To a solution of ethyl-2-(3-bromo-5-fluorobenzylidene)-3-oxobutanoate (46.8 g, 148.5 mmol) and 4-chlorobenzaldehyde (21.4 g, 152.2 mmol) in ethanol (240 mL) was added triethylamine (31 mL, 222 mmol). Nitrogen gas was bubbled through the mixture for 5 min and 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride (6 g, 22 mmol) was then added. The mixture was heated to 70 C. for 2 h under a nitrogen atmosphere. The solvent was removed under vacuum and the residual crude was dissolved in EtOAc (700 mL) and washed with 1 M aqueous HCl (130 mL), water (2*150 mL) and brine (2*20 mL). The organic extract was dried over MgSO4, filtered and concentrated under vacuum to give ethyl 2-acetyl-3-(3-bromo-5-fluorophenyl)-4-(4-chlorophenyl)-4-oxobutanoate as an orange gum (73.1 g) which was used without purification. LCMS (ESI) [M+Na]+=477.0/479.0

Molecular Weight:269.79
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:269.0641130
Monoisotopic Mass:269.0641130
Topological Polar Surface Area:52.4
Heavy Atom Count:17
Complexity:206
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes