Реакция #2467961

Уравнение реакции

water

ammonium hydroxide

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

→

product

Выход 72.0%

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

Выход 72.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Фильтрацияthe precipitated solid was filtered
3. 3
   Другоеdried
4. 4
   Другоеto give crude product, which
5. 5
   Другоеwas chromatographed over silica gel column

Методика

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)+.

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