C(#N)C.N(OC(C)(C)C)=O.N[C:12]1[S:13][CH:14]=[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:16]=1.C(Cl)(Cl)[Cl:24].CCCCCC>[Cu](Cl)Cl>[Cl:24][C:12]1[S:13][CH:14]=[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:16]=1To 200 mL of acetonitrile was added 9.7 mL (81 mmol) of t-butyl nitrite and 8.75 g (65.1 mmol) of copper(II) chloride, and 10 mL of acetonitrile containing 10.0 g (54.3 mmol) of 2-amino-4-hexylthiazole (Helvetica Chemica Acta XXXII, Fasciculus I, 35 (1949)) dissolved therein was added to this portion-wise while cooling with ice under an argon atmosphere and the temperature thereof was returned to room temperature and the mixture was stirred for 2 hours. Then, the resultant reaction mixed liquid was poured into 100 ml of chloroform/hexane mixed liquid, and the precipitate was removed by filtration. The filtrate was washed with 100 ml of a 20 wt % hydrochloric acid aqueous solution three times, then, extracted with chloroform. The resultant extraction liquid was dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure, and purified by silica gel column chromatography (development solvent:chloroform/hexane=1/1 (volumetric ratio)), to obtain the intended 2-chloro-4-hexylthiazole.
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