반응 #1449734

반응 방정식

(2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acid

tetrahydrofuran

triethylamine

methyl 6-aminohexanoate hydrochloride

→

title compound

수율 89.5%

(2E,4E)-6-[5-(2-Nitrophenyl)penta-2,4-dienoylamino]hexanoic acid methyl ester

수율 89.5%

반응 조건

후처리

1. 1
   기타The solvent was evaporated, to the obtained residue water (15 ml)
2. 2
   workup.ADDITIONwas added
3. 3
   여과the precipitate was filtered off
4. 4
   세척The precipitate was washed with an additional amount of water
5. 5
   기타dried

실험 절차

To a solution of (2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acid (9a) (0.44 g, 2.0 mmol) in dry tetrahydrofuran (10 ml) 1,1′-carbonyldiimidazole (0.36 g, 2.2 mmol) (Sigma-Aldrich) was added and the mixture was stirred for 1 hour at ambient temperature. To the reaction mixture triethylamine (0.30 g 3.0 mmol) and methyl 6-aminohexanoate hydrochloride (10) (0.40 g, 2.2 mmol) successively were added and the resultant suspension was stirred for 6 hour at ambient temperature. The solvent was evaporated, to the obtained residue water (15 ml) was added and the precipitate was filtered off. The precipitate was washed with an additional amount of water and dried to give the title compound (0.62 g, 89%) as a yellow solid, m.p. 115-117° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.10-1.79 (6H, m, CH2); 2.29 (2H, J=7.0 Hz, CH2); 3.17 (2H, q, J=5.6 Hz, CH2N); 3.60 (3H, s); 6.24 (1H, d, J=14.8 Hz, CH); 7.04-8.10 (8H, m, CH—CH═CH, C6H4, NH).

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