تفاعل #2467974

معادلة التفاعل

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

sodium hydroxide

HCl

→

product

المردود 38.0%

3-[(dimethylamino)diazenyl]thiophene-2-carboxylic acid

المردود 38.0%

المذيبات

methanol

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe mixture was diluted with ice cold water
2. 2
   استخلاصextracted with chloroform
3. 3
   غسيلThe combined chloroform 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 a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (200 mg, 0.93 mmol) in methanol (10 mL) was added a solution of sodium hydroxide (93 mg, 2.3 mmol) in water (2 mL) and stirred at rt for 2 h. The mixture was diluted with ice cold water and acidified with dil. HCl and extracted with chloroform. The combined chloroform 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 (80:20) as eluents to give the product as an off-white solid (70 mg, 38%), mp 108-110° C. IR (neat) νmax 3402, 3082, 2923, 1708, 1218, 1116, 1066, 1016, 880, 773 cm−1; 1H NMR (400 MHz, CDCl3): δ 12.21 (1H, s), 7.47 (1H, d, J=5.2 Hz), 7.30 (1H, d, J=5.2 Hz), 3.65 (3H, s), 3.28 (3H, s); LC-MS (positive ion mode): m/z 200 (M+H)+.

المصدر