2-Thiazolemethanamine, 4,5-dimethyl- synthesis

5synthesis methods

Product Name:2-Thiazolemethanamine, 4,5-dimethyl-
CAS Number:89601-18-3
Molecular formula:C6H10N2S
Molecular Weight:142.22

2-Thiazolecarboxaldehyde, 4,5-dimethyl-, oxime

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Yield:-

Reaction Conditions:

Stage #1: 4,5-dimethylthiazole-2-carbaldehyde oximewith acetic acid;zinc at 20;
Stage #2: with hydrogenchloride;ammonium chloride in water;toluene; pH=2;
Stage #3: with sodium hydroxide in water; pH=10;

Steps:

1.d

Representative procedure for the conversion of thiazole-2-carbaldehyde derivatives into (1,3-thiazol-2-yl)methylamine derivatives. Under argon, a solution of 4,5-dimethyl-1,3-thiazole-2-carbaldehyde (644.9 mg, 4.57 mmol), hydroxylamine hydrochloride (648.1 mg, 9.143 mmol) and sodium methoxide (493.7 mg, 9.14 mmol) in ethanol (9 mL) was stirred at room temperature overnight. The white solid was filtered off, rinsed with methanol and the solution was evaporated. The crude oxime was dissolved in acetic acid (25 mL), zinc dust (1.8 g, 27.5 mmol) was added portionwise at room temperature and the reaction mixture was stirred at room temperature for 3 hours. The mixture was then filtered over a pad of celite and rinsed with methanol. Toluene was added and the filtrate was concentrated. An aqueous solution of ammonium chloride was added, the solution was acidified to pH = 2 with hydrochloric acid 1N and extracted with diethyl ether and ethyl acetate. These organic layers were discarded. The aqueous layer was basified with aqueous sodium hydroxide to pH = 10, and then extracted with diethyl ether and ethyl acetate. Combined organic extracts were dried over sodium sulfate, filtered and evaporated to give crude (4,5-dimethyl-1,3-thiazol-2-yl)methylamine (321.7 mg, 49%) as a pale yellow oil which was used in the next steps without purification. ESI-MS m/z 143 (M+ H)⁺.

References:

EP2141164,2010,A1 Location in patent:Page/Page column 10-11

10200-59-6 Synthesis