تفاعل #2467978

معادلة التفاعل

water

methyl amine

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

→

solid

المردود 76.0%

{3-[(dimethylamino)diazenyl](2-thienyl)}-N-methylcarboxamide

المردود 76.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   استخلاصthe solution was extracted with chloroform (3×100 mL)
3. 3
   غسيلThe combined chloroform layer was washed with water, brine
4. 4
   تجفيفdried over sodium sulfate
5. 5
   ترشيحThe solution was filtered
6. 6
   أخرىevaporated the solvent
7. 7
   أخرىThe residue was chromatographed over silica gel column
8. 8
   أخرىto give the product, which
9. 9
   أخرىwas recrystallized from chloroform-hexane

الإجراء التجريبي

To an ice cold (0-5° C.) solution of methyl amine (3 mL) in THF (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (500 mg) in THF (5 mL) for 5 min and stirred at rt for 36 h. The solution was poured into ice cooled water and the solution was extracted with chloroform (3×100 mL). The combined chloroform 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 chloroform-methanol (98:2) as eluents to give the product, which was recrystallized from chloroform-hexane gave the product as a pale orange color solid (380 mg, 76%), mp 98-102° C. IR (neat) νmax 3297, 3082, 2929, 1637, 1380, 1348, 1299, 1221, 1109, 1016, 882, 776 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.35 (1H, br s), 7.29 (1H, d, J=5.2 Hz), 7.27 (1H, d, J=5.2 Hz), 3.57 (3H, br s), 3.21 (3H, br s), 3.00 (3H, d, J=4.8 Hz); LC-MS (positive ion mode): m/z 213 (M+H)+.

المصدر