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Volumn , Issue 11, 2008, Pages 1633-1634

Efficient one-pot synthesis of unsymmetrical 2-thioparabanic acids from oxalyl chloride, benzoyl isothiocyanate, and primary amines

(3) Yavari, Issa a Souri, Sanaz a Sirouspour, Mehdi a

a TARBIAT MODARES UNIVERSITY (Iran)

Author keywords

2 thioparabanic acid; Multicomponent reaction; Oxalyl chloride; Primary amines

Indexed keywords

2 THIOPARABANIC ACID; ACID; AMINE; BENZOYL ISOTHIOCYANATE; CHLORIDE; ISOTHIOCYANIC ACID DERIVATIVE; OXALYL CHLORIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 48249086579 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077872 Document Type: Article

Times cited : (17)

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- 1-Benzyl-2-thioxodihydro-1H-imidazole-4,5-dione (4a) To a stirred solution of benzoyl isothiocyanate (0.32 g, 2 mmol) and benzylamine (0.20 g, 2 mmol) in CH2C12 (10 mL) was added oxalyl chloride (0.25 g, 2 mmol) at r.t. The reaction mixture was then stirred for 12 h. The solvent was removed under reduced pressure and the viscous residue was purified by flash column chromatography on SiO12 (Merck 230-400 mesh) using hexane-EtOAc as eluent to give 4a as yellow powder; mp 151-153 °C, yield 0.30 g (70, IR (KBr, vmax, 3220, 1764, 1735, 1666, 1441, 1340 cm-1. 1H NMR (500 MHz, CDC13, δ, 5.10 (2 H, s, NCH2, 7.28 (1 H, d, 3J= 7.1 Hz, CH, 7.32 (2 H, t, 3J= 7.6 Hz, CH, 7.41 (2 H, d, 3J= 7.3 Hz, CH, 11.71 (1 H, br s, NH) ppm. 13C NMR (125 MHz, CDC13, δ, 45.0 (NCH2, 128.6 CH
- 2S (220.24): C, 54.53; H, 3.66; N, 12.72. Found: C, 54.41; H, 3.70; N, 12.65.

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