A novel synthetic methodology for preparation of thiocarbohydrazone by reacting thiocarbohydrazide with 1-acetyl-5-chloroisatin is described. The title compound was prepared by condensation of thiocarbohydrazide and substituted isatin in aqueous ethanol. The newly synthesized compound was characterized using 1H-NMR, 13C-NMR, FT-IR and mass spectrometry.

Molbank 2013, 2013(2), M798; doi:10.3390/M798

Short Note

N"-[(3Z)-1-Acetyl-5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]thiocarbonohydrazide

Nataša Ristovska * , Frosa Anastasova and Marina Stefova

http://www.mdpi.com/1422-8599/2013/2/M798

Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University, Gazi baba bb, 1000 Skopje, Macedonia

* Author to whom correspondence should be addressed.

 E-Mail: ristovska.natasha@on.net.mk;

Tel. +38-923-249-914; Fax +38-923-228-141.

Received: 8 February 2013; Accepted: 9 April 2013 / Published: 16 April 2013

N"-[(3Z)-1-Acetyl-5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]thiocarbonohydrazide. A solution

of thiocarbohydrazide (0.53 g, 5 mmol) in 10 mL hot water was added in small aliquots to 1-acetyl-5-

chloroindoline-2,3-dione (1.12 g, 5 mmol) in 30 mL of ethanol. The mixture was refluxed for five

minutes and then was stirred overnight at room temperature. The resulting yellow precipitate was

collected by vacuum filtration, washed with ethanol/water solution (3:1, v/v) and air dried. Bright

yellow solid was obtained after recrystallization from ethanol in typical yield of 70%.

M.p.: 252–253 C

FTIR (KBr, cm−1): (NH) 3319, 3192, 3174, 3140, (CO) 1672, (CO) lactam 1605. 

1H-NMR (200 MHz, DMSO-d6): δ/ppm 14.15 (s, 1H, NH, C=N-NH-CS), 9.54 (s, 1H, NH CSNHNH2),

6.62 (s, 2H, CSNHNH2), 7.9–7.47 (m, 3H, Ar-H), 2.01 (s, 3H, CH3CO).

13C-NMR (200 MHz, DMSO-d6): /ppm 182.87 (C=S), 168.68 (C=O, NCOCH3), 148.64 (C=O,

lactam), 143.34 (C=N), 136.38 (CAr), 130.71 (CAr), 130.18 (CAr), 127.59 (CAr), 125.63 (CAr), 125.00

(CAr), 24.15 (NCOCH3).

MS m/z: [M−H]− at 310 (100%) represents the molecular ion with formula C11H10

35ClN5O2S (minusone H due to the negative ionization mode). The corresponding isotopic peak (for 37Cl) was observed at m/z 312 (26.1%).MS2 m/z: 236 (100%), 237 (7.5%), 238 (28.0%), 208 (1.5%), 194 (1%), 166 (1.5%).

MS3 m/z: 194 (91.1%), 195 (10.2%), 196 (20.5%), 166 (100%), 167 (11.7%), 168 (22.6%).

Anal. Calcd. for C11H10ClN5O2S (311.75): C, 42.38; H, 3.23; N, 22.46. Found: C, 42.22; H, 3.16; N, 22.25. 

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