反応 #2467973

反応方程式

water

ammonium hydroxide

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

→

solid

収率 8.0%

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

収率 8.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   抽出extracted with chloroform
3. 3
   洗浄The combined organic layer was washed with water, brine
4. 4
   乾燥dried over sodium sulfate
5. 5
   ろ過The solution was filtered
6. 6
   その他evaporated the solvent
7. 7
   その他The residue was chromatographed over silica gel column
8. 8
   その他to give the product
9. 9
   その他The crude product was recrystallized from chloroform-hexane

実験手順

To an ice cold (0-5° C.) solution of ammonium hydroxide (80 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]-5-phenylthiophene-2-carboxylate (2.2 g) in THF (15 mL) for 5 min followed by catalytic amount of PEG-400 and the mixture was stirred at rt for 36 h. The solution was poured into ice cooled water and extracted with chloroform. 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 chloroform-methanol (94:6) as eluents to give the product. The crude product was recrystallized from chloroform-hexane to give the product as a yellow color solid (170 mg, 8%), mp 220-222° C. IR (neat) νmax, 3343, 2922, 2855, 1642, 1595, 1221, 1023, 880, 841 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.30 (1H, br s), 7.64-7.66 (2H, m), 7.53 (1H, s), 7.30-7.41 (3H, m), 6.34 (1H, br s), 3.59 (3H, s), 3.20 (3H, s); 13C NMR (100 MHz, CDCl3): δ 164.7, 151.1, 146.7, 133.9, 128.9, 128.5, 125.8, 125.4, 114.7, 43.6, 36.5; LC-MS (positive ion mode): m/z 297 (M+Na)+.

出典