반응 #2467974

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

sodium hydroxide

HCl

→

product

수율 38.0%

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

수율 38.0%

용매

methanol

water

반응 조건

후처리

1. 1
   workup.ADDITIONThe mixture was diluted with ice cold water
2. 2
   추출extracted with chloroform
3. 3
   세척The combined chloroform 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

실험 절차

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)+.

출처