ChemicalBook CAS DataBase List N-(2-Chlorophenyl)benzenecarbohydrazonoylchloride

N-(2-Chlorophenyl)benzenecarbohydrazonoylchloride synthesis

7synthesis methods

Product Name:N-(2-Chlorophenyl)benzenecarbohydrazonoylchloride
CAS Number:26946-54-3
Molecular formula:C13H10Cl2N2
Molecular Weight:265.14

Benzaldehyde,2-(2-chlorophenyl)hydrazone

2989-40-4
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N-(2-Chlorophenyl)benzenecarbohydrazonoylchloride

26946-54-3
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Yield:26946-54-3 84%

Reaction Conditions:

with N-chloro-succinimide;dimethylsulfide in dichloromethane at -78; for 1 h;

Steps:

1 4.1.2 General procedure for the synthesis of hydrazonoyl chlorides

General procedure: To NCS (3.0 equiv) in CH₂Cl₂ (3.5mL/mmol of hydrazone) at 0°C was added methyl sulfide (6.0 equiv) over 5min. After stirring for 15min, the reaction was further cooled to-78°C. Then the corresponding hydrazone 10 (1.0 equiv) dissolved in CH₂Cl₂ (1mL/mmol of hydrazone) was added. The reaction was stirred at-78°C for 1h, and then slowly allowed to warm to room temperature over 3h. The reaction was quenched by addition of cold water. The organic layer was then washed with brine (1x), saturated sodium sulfite aqueous solution (2x), and water. The organic layer was dried over anhydrous Na₂SO₄, filtered, and concentrated to afford the corresponding hydrazonoyl chloride (adapted from Ref.[32]). Spectroscopic characteristics of hydrazonoyl chlorides 7a [38], 7b-d [32], 7f [32], and 7g [39] have been reported before. 4.1.2.1 N'-(2-chlorophenyl)benzohydrazonoyl chloride (7e) Pink solid (1.9g, 84% yield). ¹H NMR (300MHz, CDCl₃) δ (ppm): 8.57 (br s, 1H, NH), 7.98-7.91 (m, 2H), 7.60 (dd, J=8.2, 1.5Hz, 1H), 7.47-7.37 (m, 3H), 7.33 (dd, J=8.0, 1.4Hz, 1H), 7.30-7.22 (m, 1H), 6.87 (ddd, J=7.9, 7.5, 1.5Hz, 1H); ¹³C NMR (75MHz, CDCl₃) δ (ppm): 139.52 (Cq), 134.31 (Cq), 129.71 (CH), 129.42 (CH), 128.59 (2CH), 128.12 (CH), 127.37 (Cq), 126.74 (2CH), 121.23 (CH), 118.14 (Cq), 114.75 (CH).

References:

Ribeiro, Carlos J.A.;Nunes, Rute C.;Amaral, Joana D.;Gon?alves, Lídia M.;Rodrigues, Cecília M.P.;Moreira, Rui;Santos, Maria M.M. [European Journal of Medicinal Chemistry,2017,vol. 140,p. 494 - 509]