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ChemicalBook CAS DataBase List 2-Acetylamino-4-methyl-thiazole-5-carboxylic acid

2-Acetylamino-4-methyl-thiazole-5-carboxylic acid synthesis

3synthesis methods
-

Yield: 91%

Reaction Conditions:

with pyridine in tetrahydrofuran at 0 - 20; for 21 h;

Steps:

5.1.2 2-(Acetylamino)-4-methyl-1,3-thiazole-5-carboxylic acid (7)
To a suspension of 6 (500mg, 3.20mmol) in tetrahydrofuran (20mL) were added pyridine (1.30mL, 16.0mmol) and acetyl chloride (0.60ml, 7.90mmol) at 0°C, and the reaction mixture was stirred for 21h at room temperature. After the volatiles of the mixture were removed in vacuo, water was poured into the residue, and the suspension was stirred for 1h. The resulting precipitate was collected by filtration, washed with water and dried in vacuo to yield 7 (585mg, 91%) as a colorless powder. 1H NMR (200MHz, DMSO-d6) δ 2.15 (s, 3H), 2.52 (s, 3H), 12.35 (br s, 1H); MS (ESI): m/z 201 [M+H]+, 223 [M+Na]+, 199 [M-H]-.

References:

Oka, Yusuke;Yabuuchi, Tetsuya;Oi, Takahiro;Kuroda, Shoichi;Fujii, Yasuyuki;Ohtake, Hidenori;Inoue, Tomoyuki;Wakahara, Shunichi;Kimura, Kayo;Fujita, Kiyoko;Endo, Mayumi;Taguchi, Kyoko;Sekiguchi, Yoshinori [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 24,p. 7578 - 7583]