Reaction #2467966

Reaction equation

water

ammonium hydroxide

methyl 3-[(dimethylamino)diazenyl]-5-nitrothiophene-2-carboxylate

→

solid

Yield 26.0%

3-[(Dimethylamino)diazenyl]-5-nitrothiophene-2-carboxamide

Yield 26.0%

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Extractionextracted with ethyl acetate (3×100 mL)
3. 3
   WashThe combined organic layer was washed with water, brine
4. 4
   Dryingdried over sodium sulfate
5. 5
   FiltrationThe solution was filtered
6. 6
   Otherevaporated the solvent
7. 7
   OtherThe residue was chromatographed over silica gel column

Procedure

To an ice cold (0-5° C.) solution of ammonium hydroxide (35 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]-5-nitrothiophene-2-carboxylate (400 mg) in THF (10 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and extracted with ethyl acetate (3×100 mL). The combined organic 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 hexane-ethyl acetate (50:50) as eluents to give the product as a yellow color solid (90 mg, 26%), mp 240-246° C. 1H NMR (400 MHz, DMSO-d6): δ 8.22 (1H, s), 8.05 (1H, s), 7.91 (1H, s), 3.63 (3H, s), 3.26 (3H, s); LC-MS (positive ion mode): m/z 266 (M+Na)+.

Source