Reaktion #2467963

Reaktionsgleichung

water

ammonium hydroxide

methyl 3-[(dimethylamino)diazenyl]-4-bromothiophene-2-carboxylate

→

product

Ausbeute 53.0%

3-[(Dimethylamino)diazenyl]-4-bromothiophene-2-carboxamide

Ausbeute 53.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Extraktionextracted with ethyl acetate (3×50 mL)
3. 3
   WaschenThe combined EtOAc layer was washed with water, brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   FiltrationThe solution was filtered
6. 6
   Sonstigeevaporated the solvent
7. 7
   SonstigeThe residue was chromatographed over silica gel column

Vorschrift

To an ice cold (0-5° C.) solution of ammonium hydroxide (10 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]-4-bromothiophene-2-carboxylate (500 mg) in THF (5 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and extracted with ethyl acetate (3×50 mL). The combined EtOAc 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 as an off-white solid (250 mg, 53%), mp 194-196° C. 1H NMR (400 MHz, DMSO-d6): δ 7.85 (1H, s), 7.75 (1H, br s), 7.56 (1H, br s), 3.56 (3H, br s), 3.21 (3H, br s); LC-MS (positive ion mode): m/z 277, 279 (M+H)+.

Quelle