Reaction #2467961

Reaction equation

water

ammonium hydroxide

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

→

product

Yield 72.0%

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

Yield 72.0%

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Filtrationthe precipitated solid was filtered
3. 3
   Otherdried
4. 4
   Otherto give crude product, which
5. 5
   Otherwas chromatographed over silica gel column

Procedure

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)+.

Source