反应 #2467961

反应方程式

water

ammonium hydroxide

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

→

product

收率 72.0%

3-[(Dimethylamino)diazenyl]thiophene-2-carboxamide

收率 72.0%

溶剂

THF

反应条件

后处理

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   过滤the precipitated solid was filtered
3. 3
   其他dried
4. 4
   其他to give crude product, which
5. 5
   其他was chromatographed over silica gel column

实验过程

To an ice cold (0-5° C.) solution of ammonium hydroxide (20 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (600 mg) in THF (5 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and the precipitated solid was filtered and dried to give crude product, which was chromatographed over silica gel column using chloroform-methanol (98:2) as eluents to give the product as an off-white solid (400 mg, 72%), mp 168-170° C. IR (neat) νmax 3337, 3172, 2923, 1636, 1599, 1348, 1219, 1117, 884, 771 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.28 (2H, br s), 7.35 (1H, d, J=5.6 Hz), 7.31 (1H, d, J=5.6 Hz), 3.58 (3H, br s), 3.20 (3H, br s); LC-MS (positive ion mode): m/z 221 (M+Na)+.

来源