Propanedinitrile, 2-[2-[(1E)-2-(4-aminophenyl)ethenyl]-4H-1-benzopyran-4-ylidene]- synthesis

8synthesis methods

Product Name:Propanedinitrile, 2-[2-[(1E)-2-(4-aminophenyl)ethenyl]-4H-1-benzopyran-4-ylidene]-
CAS Number:1430329-73-9
Molecular formula:C20H13N3O
Molecular Weight:311.34

(E)-2-(2-(4-azidostyryl)-4H-chromen-4-ylidene)malononitrile

1430329-72-8
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Propanedinitrile, 2-[2-[(1E)-2-(4-aminophenyl)ethenyl]-4H-1-benzopyran-4-ylidene]-

1430329-73-9
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Yield:1430329-73-9 61.4%

Reaction Conditions:

with sodium hydrogen sulfide in water;acetonitrile; pH=7.4; for 1 h;

Steps:

4.2.6. Synthesis of DCMCeNH2

A solution of 1 (30 mg, 0.089 mmol) in dry CH3CN (50 mL) was added NaHS (996.8 mg, 17.8 mmol) which was dissolved in 5 mL water. The reaction mixture was stirred at temperature for 1 h. Then the mixture was ltered to get a brownish solid without further purication. Yield: 17 mg (61.4%). 1H NMR (CDCl3, 500 MHz) d 8.92 (d, J 8.5 Hz, 1H), 7.72 (t, J 8 Hz, 1H), 7.57e7.53 (m, 2H), 7.47e7.42 (m, 3H), 6.81 (s, 1H), 6.70 (d, J 8.5 Hz, 2H), 6.62 (d, J 16 Hz, 1H), 4.05 (s, 2H), 13C NMR (CDCl3, 500 MHz) d 160.2, 153.0, 152.6, 152.5, 141.1, 135.5, 131.2, 126.4, 125.0, 122.8, 119.4, 118.3, 117.7, 116.9, 114.3, 112.9, 105.2, 57.8. HRMS (ESI) calcd for C20H14N3O [MH] 312.1137, found 312.1135.

References:

Zheng, Yi;Zhao, Miao;Qiao, Qinglong;Liu, Huiying;Lang, Haijing;Xu, Zhaochao [Dyes and Pigments,2013,vol. 98,# 3,p. 367 - 371]