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2-Amino-5-iodo-4-trifluoromethylthiazole (1.2 g) was dissolved in pyridine (2 ml) and thiophene-2-carbonyl chloride (0.80 g) was added at room temperature with stirring. The mixture was stirred for 6 hr at room temperature. The mixture was poured into ice water and acidified with aqueous hydrochloric acid then extracted with chloroform. The chloroform layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. The solid thus obtained was recrystallized from methanol to give N-(5-iodo-4-trifluoromethylthiazol-2-yl)thiophene-2-carboxamide (1.2 g), m. p. 184-185 C.
2-Amino-5-iodo-4-trifluoromethylthiazole (1.0 g) was dissolved in pyridine (2 ml) and 3,5-bis-trifluoromethylbenzoylchloride (0.95 g) was added at room temperature with stirring. The mixture was stirred for 6 hr at room temperature. The mixture was poured into ice water and acidified with aqueous hydrochloric acid then extracted with chloroform. The chloroform layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. The solid thus obtained was recrystallized from methanol to give N-(5-iodo-4-trifluoromethylthiazol-2-yl)-3,5-bis-trifluoromethylbenzamide (1.3 g), m. p. 172-173 C.
N-(5-Iodo-4-trifluoromethylthiazol-2-yl)-4-trifluoromethyl-benzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With pyridine; at 20.0℃; for 24.0h;
2-Amino-5-iodo-4-trifluoromethylthiazole (2.5 g) was dissolved in pyridine (8 ml) and 4-trifluoromethylbenzoylchloride (1.8 g) was added at room temperature with stirring. The mixture was stirred for 1 day at room temperature. The mixture was poured into ice water and acidified with aqueous hydrochloric acid then extracted with chloroform. The chloroform layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. The solid thus obtained was recrystallized from methanol to give N-(5-iodo-4-trifluoromethylthiazol-2-yl)-4-trifluoro-methylbenzamide (2.9 g), m. p. 197-198 C.
2-Amino-5-iodo-4-trifluoromethylthiazole (0.8 g) was dissolved in pyridine (3 ml) and 2,6-dichlorobenzoylchloride (0.6 g) was added at room temperature with stirring. The mixture was stirred for 1 day at room temperature. The mixture was poured into ice water and acidified with aqueous hydrochloric acid then extracted with chloroform. The chloroform layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. The solid thus obtained was recrystallized from methanol to give N-(5-iodo-4-trifluoromethylthiazol-2-yl)-2,6-dichlorobenzamide (0.9 g), m. p. 157-159 C.
With N-iodo-succinimide; In acetonitrile; at 20℃; for 6h;
2-Amino-4-trifluoromethylthiazole (10 g) was dissolved in acetonitrile (100 ml) and N-iodosuccinimide (14.7 g) was added at room temperature with stirring. The mixture was refluxed for 6 hr and the solvent was removed under reduced pressure. The residue was dissolved in chloroform and washed with cold diluted aqueous sodium hydroxide. The chloroform layer was dried over magnesium sulfate and the solvent was removed under reduced pressure to give crude 2-Amino-5-iodo-4-trifuloromethylthiazole (16 g). It was recrystallized from n-hexane-benzene (1:1 mixture) as pale orange prisms (10.9 g), m. p. 108-109° C.
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