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ChemicalBook CAS DataBase List 2-(Trifluoromethyl)-4-thiazolemethanamine
852854-39-8

2-(Trifluoromethyl)-4-thiazolemethanamine synthesis

1synthesis methods
852854-38-7 Synthesis
4-(BroMoMethyl)-2-(trifluoroMethyl)thiazole

852854-38-7
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2-(Trifluoromethyl)-4-thiazolemethanamine

852854-39-8
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Yield:852854-39-8 52%

Reaction Conditions:

Stage #1: 4-(bromomethyl)-2-(trifluoromethyl)thiazolewith potassium phtalimide in DMF (N,N-dimethyl-formamide) at 20;
Stage #2: with hydrazine in tetrahydrofuran;ethanol at 20;

Steps:

37

Potassium phthalimide (495 mg, 2.7 mmol) was added to a solution of Description 36 (470 mg, 1.9 mmol) in N, N-dimethylformamide (anhydrous, 7 ml). The resulting suspension was stirred at room temperature overnight. The resulting solid was filtered, and the filtrate extracted into ethyl acetate, washed with water, dried overMgS04, evaporated in vacuo to give a white solid (520 mg, 1.67 mmol). This was dissolved in tetrahydrofuran/ethanol (10 ml/15 ml), hydrazine hydrate(600jj. l, 10.4 mmol) added, and the reaction stirred at room temperature overnight. To the resulting suspension was added hydrochloric acid (ION, 10 ml) and the mixture filtered. The filtrate was basified to pH 10 with solidNaOH, and extracted into DCM. The DCM layer was dried overMgS04, evaporated invacuo to give the title compound as a yellow oil(170 mg, 52%).'H NMR (400 MHz, DMSO) 8 7.88(1H, s), 3.88 (2H, s). M/z (ES+) 183 (M+H+).

References:

WO2005/49613,2005,A1 Location in patent:Page/Page column 51