تفاعل #2467960

معادلة التفاعل

K2CO3

dimethylamine

methyl 3-aminothiophene-2-carboxylate

HCl

NaNO2

→

solid

المردود 88.5%

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

المردود 88.5%

المذيبات

H2O

H2O

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred at 0-5° C. for 1 h
2. 2
   workup.ADDITIONpoured into ice cold water
3. 3
   استخلاصThe solution was extracted with chloroform (3×30 mL)
4. 4
   غسيلThe combined CHCl3 layer was washed with water, brine
5. 5
   تجفيفdried over sodium sulfate
6. 6
   ترشيحThe solution was filtered
7. 7
   أخرىevaporated the solvent
8. 8
   أخرىThe residue was chromatographed over silica gel column

الإجراء التجريبي

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)+.

المصدر