반응 #2467978

반응 방정식

water

methyl amine

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

→

solid

수율 76.0%

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

수율 76.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   추출the solution was extracted with chloroform (3×100 mL)
3. 3
   세척The combined chloroform layer was washed with water, brine
4. 4
   건조dried over sodium sulfate
5. 5
   여과The solution was filtered
6. 6
   기타evaporated the solvent
7. 7
   기타The residue was chromatographed over silica gel column
8. 8
   기타to give the product, which
9. 9
   기타was recrystallized from chloroform-hexane

실험 절차

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)+.

출처