ChemicalBook CAS DataBase List 4-TRIFLUOROMETHYL-THIAZOL-2-YLAMINE

4-TRIFLUOROMETHYL-THIAZOL-2-YLAMINE synthesis

7synthesis methods

Product Name:4-TRIFLUOROMETHYL-THIAZOL-2-YLAMINE
CAS Number:349-49-5
Molecular formula:C4H3F3N2S
Molecular Weight:168.14

431-35-6

17356-08-0

349-49-5

General procedure for the synthesis of 2-amino-4-trifluoromethylthiazole from 3-bromo-1,1,1-trifluoroacetone and thiourea: Thiourea (4.0 g, 52.3 mmol) and 3-bromo-1,1,1-trifluoropropan-2-one (5.5 mL, 10 g, 52.3 mmol) were added to ethanol (100 mL) and the reaction was heated for 2 hours at 50 °C. After completion of the reaction, it was cooled to room temperature and the reaction solution was concentrated to dryness. The residue was dissolved in water and the pH was adjusted with 2 M NaOH solution to >12. Subsequently, four extractions were performed with ether. The organic extracts were combined, dried with sodium sulfate, filtered and concentrated in vacuum. The resulting crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to afford 2-amino-4-trifluoromethylthiazole (6.9 g, 79% yield). es/MS m/z 169 (M + 1)+.

431-35-6 Synthesis

431-35-6
230 suppliers
$10.00/5 g

17356-08-0
2 suppliers
inquiry

349-49-5
168 suppliers
$15.00/250mg

Yield: 79%

Reaction Conditions:

Stage #1:3-bromo-1,1,1-trifluoroacetone;thiourea in ethanol at 50; for 2 h;
Stage #2: with sodium hydroxide;water; pH=> 12

Steps:

21
Preparation 214-Trifluoromethyl-thiazole-2-ylamineAdd thiourea (4.0 g, 52.3 mmol) and 3-bromo-l,l,l-trifluoropropan-2-one (5.5 mL, 10 g, 52.3 mmol) to ethanol (100 mL) and heat at 50 ⁰C for 2 h. Cool to room temperature and concentrate to dryness. Dissolve the residue in water and adjust the pH to >12 with 2 M NaOH. Extract with diethyl ether (4*). Dry the combined organic extracts with sodium sulfate, filter, and concentrate under vacuum. Purify the resulting material by silica gel chromatography (CH₂Cl₂) to obtain the title compound (6.9 g, 79%). ES/MS m/z 169 (M+ 1)⁺.

References:

ELI LILLY AND COMPANY WO2008/36579, 2008, A1 Location in patent:Page/Page column 43