C-(4-PHENYL-THIAZOL-2-YL)-METHYLAMINE synthesis

3synthesis methods

Product Name:C-(4-PHENYL-THIAZOL-2-YL)-METHYLAMINE
CAS Number:90916-45-3
Molecular formula:C10H10N2S
Molecular Weight:190.26

N-(4-PHENYL-THIAZOL-2-YLMETHYL)-BENZAMIDE

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Yield: 77%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;water at 100; for 24 h;

Steps:

52 (4-Phenylthiazol-2-yl)methanamine
6N HCl (4.5 mL) was added to a solution of N-((4-phenylthiazol-2-yl)methyl)benzamide (150 mg, 0.51 mmol) in dioxane (10 mL) and the reaction mixture was stirred at 100 °C for 24 h (reaction monitored by TLC, eluant CHCl₃/MeOH).
Reaction mixture was concentrated under reduced pressure and the residue was dissolved in water.
The aqueous layer was washed twice with EtOAc.
The pH of the aqueous layer was then adjusted to pH ∼9 using 10% NaHCO₃ and the organic product was extracted with EtOAc.
The organic layer was washed with brine and concentrated under reduced pressure to yield (4-phenylthiazol-2-yl)methanamine (75 mg, yield 77%) as orange colored liquid, which was carried through without further purification. ¹H NMR (300MHz, CDCl₃) δ 7.91 - 7.88 (m, 2H), 7.45 - 7.40 (m, 3H), 7.36 - 7.31 (m, 1 H), 4.25 (br s, 2H), 3.79 - 3.75 (m, 1 H), 3.68 - 3.63 (m, 1 H). MS (ESI) m/z: Calculated for C₁₀H₁₀N₂S: 190.06; found: 191.2 (M+H)⁺.

References:

Tempero Pharmaceuticals, Inc.;BALOGLU, Erkan;GHOSH, Shomir;LOBERA, Mercedes;SCHMIDT, Darby EP2533783, 2015, B1 Location in patent:Paragraph 0497-0498

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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