ChemicalBook CAS DataBase List 1-(4-HYDROXYPHENYL)-2-THIOUREA

1-(4-HYDROXYPHENYL)-2-THIOUREA synthesis

12synthesis methods

Product Name:1-(4-HYDROXYPHENYL)-2-THIOUREA
CAS Number:1520-27-0
Molecular formula:C7H8N2OS
Molecular Weight:168.22

333-20-0
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$13.50/100G

123-30-8 Synthesis

123-30-8
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1520-27-0
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$15.00/250mg

Yield: 60%

Reaction Conditions:

Stage #1:4-amino-phenol with hydrogenchloride in water for 0.5 h;Inert atmosphere;Reflux;
Stage #2:potassium thioacyanate in waterInert atmosphere;Reflux;

Steps:

Preparation of aryl thiourea (2)
The published procedure was followed with minor modifications¹. A mixture of commercial 4-hydroxy aniline (1) (10.9 g, 0.1 mol), concentrated HCl (9.0 mL) and water (25 mL) were taken in a 100 cc round bottom flask and the content was refluxed for 30 min. The resulting reaction solution was cooled to room temperature and KSCN (9.7 g, 0.1 mol) was added. The reaction mixture was then refluxed for 6 h till two layers were separated out. The solution was poured over crushed ice, filtered, dried with Na₂SO₄ and crystallized from ethanol as crystalline flakes to yield (2) (10.1g, 60% yield) s the white crystals. ¹H NMR (DMSO-d₆, 400MHz) δ ppm: 9.37 (s, 1H, -OH), 9.34 (s, 1H, -NH), 7.06 (d, J = 8.4 Hz, 2H, Ar-H), 6.72 (d, J = 15.2 Hz, 2H, Ar-H).

References:

Li, Geng-Ying;Vaulina, Daria D.;Li, Jia-Je;Fedorova, Olga S.;Wang, Hsin-Ell;Liu, Ren-Shyan;Krasikova, Raisa N.;Chen, Chuan-Lin [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 15,p. 3460 - 3463] Location in patent:supporting information