4-Chlorothiazole synthesis
- Product Name:4-Chlorothiazole
- CAS Number:4175-72-8
- Molecular formula:C3H2ClNS
- Molecular Weight:119.57
4175-76-2
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4175-72-8
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Yield: 73%
Reaction Conditions:
with acetic acid;zinc
Steps:
27 Synthesis of 4,4'-bis(dodecyloxy)-2,2'-bis(trimethylstannyl)-5,5'-bithiazole
Preparation of 4-chlorothiazole (8) (procedure adapted from Bull. de la Soc. Chim. Fr. 1962, 1735): A mixture of 58 g (377 mmol) of 2,4-dichlorothiazole (7), 87 g (1.3 mol) zinc dust, and 800 mL of acetic acid was refluxed for 6 hours. Thin layer chromatography indicated complete consumption of the dichloride. The mixture was cooled to room temperature and filtered. The filter cake was washed with 3*50 mL of acetic acid. The filtrate was poured onto 2 kg of ice and was treated with about 1.3 L of 50% (w/v) aqueous NaOH until a slightly basic mixture resulted (pH 9). The mixture was extracted with diethyl ether (3*600 mL) and the combined ethereal extracts were washed successively with 500 mL of saturated aqueous NaHCO3 and 500 mL of brine. The separated organic layer was dried over K2CO3, filtered, and concentrated in vacuo to give 33 g (73% yield) of 4-chlorothiazole (8) as a colorless liquid of sufficient purity to use without further purification. 1H NMR (500 MHz) δ 8.77 (d, 1H, J=2.3 Hz), 7.19 (d, 1H, J=2.3 Hz).
References:
Watson, Mark D. US2010/252112, 2010, A1
141305-44-4
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3034-52-4
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4175-73-9
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4175-72-8
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57314-10-0
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4175-72-8
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139670-07-8
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139670-03-4
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4175-72-8
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$28.00/250mg