Reaction #2467979

Reaction equation

water

ethylenediamine

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

sodium chloride

→

product

Yield 22.0%

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

Yield 22.0%

Solvents

ethanol

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   ExtractionThe solution was extracted with THF (3×100 mL)
3. 3
   WashThe combined THF layer was washed with brine
4. 4
   Dryingdried over sodium sulfate
5. 5
   FiltrationThe solution was filtered
6. 6
   Otherevaporated the solvent
7. 7
   OtherThe residue was chromatographed over silica gel column

Procedure

To an ice cold (0-5° C.) solution of ethylenediamine (5 mL) in ethanol (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (250 mg) in ethanol (5 mL) for 5 min and stirred at rt for 24 h. The solution was poured into ice cooled water and saturated with sodium chloride. The solution was extracted with THF (3×100 mL). The combined THF layer was washed with 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 (90:10) as eluents to give the product as an off-white solid (60 mg, 22%), mp 98-100° C. 1H NMR (400 MHz, CDCl3): δ 8.65 (1H, br s), 7.30 (1H, d, J=5.2 Hz), 7.28 (1H, d, J=5.2 Hz), 3.50-3.57 (5H, m). 3.24 (3H, br s), 2.91 (2H, t, J=6.0 Hz).

Source