Water → HCID 46931261, compound

Reaction equation

[OH-].[NH4+:2].[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:9]=[C:10]([C:14]([O:16]C)=O)[Se:11][C:12]=1[CH3:13])[CH3:5].O>C1COCC1>[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:9]=[C:10]([C:14]([NH2:2])=[O:16])[Se:11][C:12]=1[CH3:13])[CH3:5]

Participants

Procedure

To an ice cold (0-5° C.) solution of ammonium hydroxide (40 mL) was added a solution of methyl 4-[(dimethylamino)diazenyl]-5-methylselenophene-2-carboxylate (550 mg) in THF (10 mL) for 5 min and stirred at rt for 40 h. The solution was poured into ice cooled water and extracted with chloroform (3×100 mL). 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 (96:4) as eluents to give the product as off-white solid (220 mg, 42%), mp 170-172° C. IR (neat) νmax 3385, 3188, 2914, 1644, 1604, 1326, 1120, 1066 cm−1; 1H NMR (400 MHz, CDCl3): δ 7.87 (1H, s, H-3), 5.67 (2H, br s, —CONH2), 3.28 (6H, br s, N(CH3)2), 2.63 (3H, s, Ar—CH3); LC-MS (positive ion mode): m/z 261, 259 (M+H)+.