반응 #2467973

반응 방정식

water

ammonium hydroxide

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

→

solid

수율 8.0%

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

수율 8.0%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   추출extracted with chloroform
3. 3
   세척The combined organic layer was washed with water, brine
4. 4
   건조dried over sodium sulfate
5. 5
   여과The solution was filtered
6. 6
   기타evaporated the solvent
7. 7
   기타The residue was chromatographed over silica gel column
8. 8
   기타to give the product
9. 9
   기타The crude product was recrystallized from chloroform-hexane

실험 절차

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)+.

출처