反応 #2467978

反応方程式

water

methyl amine

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

→

solid

収率 76.0%

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

収率 76.0%

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 chloroform (3×100 mL)
3. 3
   洗浄The combined chloroform 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 methyl amine (3 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 36 h. The solution was poured into ice cooled water and the solution was extracted with chloroform (3×100 mL). 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 chloroform-methanol (98:2) as eluents to give the product, which was recrystallized from chloroform-hexane gave the product as a pale orange color solid (380 mg, 76%), mp 98-102° C. IR (neat) νmax 3297, 3082, 2929, 1637, 1380, 1348, 1299, 1221, 1109, 1016, 882, 776 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.35 (1H, br s), 7.29 (1H, d, J=5.2 Hz), 7.27 (1H, d, J=5.2 Hz), 3.57 (3H, br s), 3.21 (3H, br s), 3.00 (3H, d, J=4.8 Hz); LC-MS (positive ion mode): m/z 213 (M+H)+.

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