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ChemicalBook CAS DataBase List PHENYLTHIOHYDANTOIN-DL-ALANINE

PHENYLTHIOHYDANTOIN-DL-ALANINE synthesis

9synthesis methods

Product Name:PHENYLTHIOHYDANTOIN-DL-ALANINE
CAS Number:4333-19-1
Molecular formula:C10H10N2OS
Molecular Weight:206.26

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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4333-19-1
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Yield: 1.34 g

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;water; pH=Ca. 2 at 0 - 160; for 0.0333333 h;Microwave irradiation;Sealed tube;

Steps:

Representative Procedure for the Preparation of 5-Methyl-3-phenyl-2-thioxo imidazolidin-4-one (3a).
General procedure: DL-Alanine 2a (623.6 mg, 7.0 mmol, 1.0 equiv) was added to a solution of phenyl isothiocyanate 1a (936.3 mg, 7.0 mmol,1.0 equiv) in 1,4-dioxane-H2O (15 mL; 1:1, v/v) at 0 oC.Et3N (1.42 g, 14.0 mmol, 2.0 equiv) was added slowly to the reaction mixture and the solution was stirred for 1 h at room temperature, followed by the addition of concentrated HCl(2.13 mL, 21.0 mmol, 3.0 equiv) at 0 oC until the pH reached~2. The reaction mixture was transferred into a 20 mL sealed reactor vessel and irradiated with stirring at 160° C for 2min. After cooling to room temperature, the reaction mixture was neutralized with saturated NaHCO3 until the pH became~6. The precipitate formed was filtered and dried to yield the desired compound 3a

References:

Yang, Seung-Ju;Lee, Jae-Min;Lee, Gee-Hyung;Kim, NaYeon;Kim, Yong-Sang;Gong, Young-Dae [Bulletin of the Korean Chemical Society,2014,vol. 35,# 12,p. 3609 - 3617] Location in patent:supporting information