反応 #2467977

反応方程式

water

ethanol amine

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

→

solid

収率 77.0%

{3-[(dimethylamino)diazenyl] (2-thienyl)}-N-(2-hydroxyethyl)-carboxamide

収率 77.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   抽出the solution was extracted with ethyl acetate (3×50 mL)
3. 3
   洗浄The combined EtOAc 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, which
9. 9
   その他was recrystallized from chloroform-hexane

実験手順

To an ice cold (0-5° C.) solution of ethanol amine (5 mL) in THF (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (500 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 solution was extracted with ethyl acetate (3×50 mL). The combined EtOAc 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 (95:5) as eluents to give the product, which was recrystallized from chloroform-hexane gave the product as a pale orange color solid (430 mg, 77%), mp 118-122° C. IR (neat) νmax, 3397, 3278, 2926, 1621, 1353, 1298, 1220, 1083, 1007, 882, 775 cm−1;

出典