反応 #2467960

反応方程式

K2CO3

dimethylamine

methyl 3-aminothiophene-2-carboxylate

HCl

NaNO2

→

solid

収率 88.5%

Methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate

収率 88.5%

溶媒

H2O

H2O

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at 0-5° C. for 1 h
2. 2
   workup.ADDITIONpoured into ice cold water
3. 3
   抽出The solution was extracted with chloroform (3×30 mL)
4. 4
   洗浄The combined CHCl3 layer was washed with water, brine
5. 5
   乾燥dried over sodium sulfate
6. 6
   ろ過The solution was filtered
7. 7
   その他evaporated the solvent
8. 8
   その他The residue was chromatographed over silica gel column

実験手順

To a solution of methyl 3-aminothiophene-2-carboxylate (0.5 g, 3.18 mmol) and conc. HCl (1.3 mL, 12.73 mmol) in H2O (7.5 mL) was added NaNO2 (0.24 g, 3.50 mmol) in portions for 5 min at 0° C. After stirring for 0.5 h at 0-5° C., the reaction mixture was added to the solution of K2CO3 (1.66 g, 12.09 mmol) and dimethylamine (1.3 mL, 40%, 11.46 mmol) in H2O (9 mL) at 0° C. The mixture was stirred at 0-5° C. for 1 h and poured into ice cold water. The solution was extracted with chloroform (3×30 mL). The combined CHCl3 layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-EtOAc (80:20) as eluents to give the product as pale orange color solid (600 mg, 88%), mp 74-76° C. 1H NMR (400 MHz, CDCl3): δ 7.33 (1H, d, J=5.6 Hz), 7.24 (1H, d, J=5.6 Hz), 3.87 (3H, s), 3.52 (3H, s), 3.29 (3H, s); LC-MS (positive ion mode): m/z 214 (M+H)+.

出典