関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Bromide ion | HCID 259 | — |
| 反応物 | Nitrogen | HCID 947 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 4-nitro-1H-pyrazole | HCID 16376 | — |
| 反応物 | Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate | HCID 10822129 | — |
| 溶媒 | Acetone | HCID 180 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 4-(4-Nitro-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester | HCID 66928895 | — |
反応手順
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-chloromethyl-thiazole-2-carboxylic acid ethyl ester (1.84 g, 8.93 mmol) in acetone (20.0 mL) was treated, under inert atmosphere (N2) with K2CO3 (6.23 g, 44.66 mmol) followed by 4-nitro-1H-pyrazole (1.00 g, 8.93 mmol) and TBA bromide (576 mg, 1.79 mmol). The resulting mixture was stirred at rt overnight. Water (40 mL), followed by EA (50 mL) were added. The aq. layer was extracted with EA (50 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound as a yellow oil. TLC: rf (50:50 hept-EA)=0.30. LC-MS-conditions 02: tR=0.90 min; [M+H]+=283.25.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08288419B2 |
|---|
| 出典データセット | uspto-grants-2012_10 |
|---|
| ORD ID | ord-385828603fc9419ea257798b5641aaa9 |
|---|
| 出典メモ | uspto-grants-2012_10 |
|---|
