تفاعل #2467961

معادلة التفاعل

water

ammonium hydroxide

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

→

product

المردود 72.0%

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

المردود 72.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   ترشيحthe precipitated solid was filtered
3. 3
   أخرىdried
4. 4
   أخرىto give crude product, which
5. 5
   أخرىwas chromatographed over silica gel column

الإجراء التجريبي

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)+.

المصدر