ChemicalBook CAS DataBase List (4-CARBOXYPHENYL)THIOUREA

(4-CARBOXYPHENYL)THIOUREA synthesis

4synthesis methods

Product Name:(4-CARBOXYPHENYL)THIOUREA
CAS Number:7366-56-5
Molecular formula:C8H8N2O2S
Molecular Weight:196.23

4-[[(Benzoylamino)thioxomethyl]amino]benzoic acid

40611-30-1

7366-56-5

4-(3-Benzoylthioureido)benzoic acid (7) (10.0 mmol) was used as raw material and mixed with 10% sodium hydroxide solution (10.0 mmol) in 20 mL of water. The reaction mixture was heated to reflux for 30 min. After completion of the reaction, it was cooled to room temperature and neutralized with hydrochloric acid. The resulting solid product was collected by filtration, washed with water, dried and recrystallized from butanol to give (4-carboxyphenyl)thiourea in white powder form in 93% yield. The product was characterized by the following data: melting point >300 °C; infrared spectra (KBr, cm-1) νmax 3440, 3339, 3279, 3170, 1684, 1291; NMR hydrogen spectra (300 MHz, DMSO-d6) δ 12.72 (1H, br s, COOH), 9.96 (1H, s, NH), 7.54-7.90 (4H, m, ArH), 3.37 (1H, s, NH2); mass spectra (EI, 70 eV) m/z 196 (10), 179 (98), 162 (98), 134 (75), 120 (95), 92 (35); calculated elemental analysis values (C8H8N2O2S, 196.23): C, 48.97; H, 4.11; N 14.28; measured values: C, 48.84; H, 4.07; N, 14.24.

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Yield:7366-56-5 93%

Reaction Conditions:

with water;sodium hydroxide for 0.5 h;Reflux;

Steps:

4-thioureidobenzoic acid (8)
A mixture of 4-(3-benzoylthioureido)benzoic acid (7) (10.0 mmol) and 10% sodium hydroxide (10.0 mmol) in water (20 mL) was heated under reflux for 30 min. The reaction mixture was cooled and neutralized by HCl. The formed product was filtered off, washed with water, driedand crystallized from butanol to give a white powder in 93% yield. mp > 300 C;mmax (KBr) 3440, 3339, 3279, 3170, 1684, 1291 cm-1; dH (300 MHz, DMSO-d6) 12.72 (1H, br s, COOH), 9.96 (1H, s, NH), 7.54-7.90 (4H, m, ArH’s), 3.37 (1H, s, NH2); m/z (EI, 70 eV) 196(10), 179(98), 162(98), 134(75), 120(95), 92(35); Elem.Anal. Calcd for C8H8N2O2S (196.23): C, 48.97; H, 4.11; N, 14.28. Found: C, 48.84;H, 4.07; N, 14.24.

References:

Haggam, Reda A.;Assy, Mohamed G.;Sherif, Mohamed H.;Galahom, Mohamed M. [Research on Chemical Intermediates,2017,vol. 43,# 11,p. 6299 - 6315]

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