تفاعل #2467963

معادلة التفاعل

water

ammonium hydroxide

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

→

product

المردود 53.0%

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

المردود 53.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   استخلاصextracted with ethyl acetate (3×50 mL)
3. 3
   غسيلThe combined EtOAc layer was washed with water, brine
4. 4
   تجفيفdried over sodium sulfate
5. 5
   ترشيحThe solution was filtered
6. 6
   أخرىevaporated the solvent
7. 7
   أخرىThe residue was chromatographed over silica gel column

الإجراء التجريبي

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)+.

المصدر