ChemicalBook CAS DataBase List (2-Thiazolyl)methylamine

(2-Thiazolyl)methylamine synthesis

5synthesis methods

Product Name:(2-Thiazolyl)methylamine
CAS Number:55661-33-1
Molecular formula:C4H6N2S
Molecular Weight:114.17

171268-82-9

7732-18-5

55661-33-1

The general procedure for the synthesis of 2-thiazole-methyl-amine from the compound (CAS: 171268-82-9) and water (electrophoretic grade) is as follows: 1. Preparation of GG1 thiazol-2-yl-methylamine azide: triphenylphosphine (2.08 g, 7.9 mmol) was added to a solution of 2-azidomethyl-thiazole (1.11 g, 7.9 mmol) in tetrahydrofuran (THF, 20 mL). 2. Reduction reaction: after 1 h, water (214 μL) and ammonium hydroxide sol (0.5 mL) were added sequentially. 3. Post-treatment: The reaction mixture was stirred overnight and subsequently concentrated under vacuum and purified by fast chromatography (eluent: 5% methanol/dichloromethane) to give the title product 2-thiazolemethanamine as a tan oil (645 mg, 72% yield). 4. The product was characterized by 1H NMR (250 MHz, CDCl3) δ 7.7 (d, 1H, J = 2.0 Hz); 7.25 (d, 1H, J = 2.0 Hz); 4.2 (s, 2H); 1.7 (bs, 2H).

171268-82-9
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7732-18-5
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55661-33-1
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Yield: 72%

Reaction Conditions:

with triphenylphosphine in tetrahydrofuran

Steps:

G.G.1 Azide Reduction
Preparation GG1 Thiazol-2-yl-methylamine Azide Reduction Triphenylphosphine (2.08 g, 7.9 mmol) was added to a solution of 2-azidomethyl-thiazole (1.11 g, 7.9 mmol) in THF (20 mL). After 1 h, H₂ O (214 μL) and ammonium hydroxide sol (0.5 mL) were added sequentially. The reaction stirred overnight, was concentrated in vacuo, and purified by flash chromatography (5% methanol/methylene chloride) to afford 645 mg of the title product as a tan oil (72%). ¹ H NMR (250 MHz, CDCl₃) 6 7.7 (d, 1H, J=2.0 Hz); 7.25 (d, 1H, J=2.0 Hz); 4.2 (s, 2H); 1.7 (bs, 2H).

References:

Pfizer Inc. US5939398, 1999, A