ChemicalBook CAS DataBase List (S)-3,4-Dimethyloxazolidine-2,5-dione

(S)-3,4-Dimethyloxazolidine-2,5-dione synthesis

5synthesis methods

Product Name:(S)-3,4-Dimethyloxazolidine-2,5-dione
CAS Number:58311-53-8
Molecular formula:C5H7NO3
Molecular Weight:129.11

(2S)-2-[(methoxycarbonyl)(methyl)amino]propanoic acid

1085528-19-3

58311-53-8

Explosion-proof operation. Synthesis of (S)-3,4-dimethyloxazolidine-2,5-dione: 1 g (6.2 mmol) of the raw material (cas:1085528-19-3) was dissolved in 3 ml of dichloromethane and stirred for 5 min at 20 °C. Subsequently, 500 μl (1.1 eq.) of thionyl chloride was added. The reaction mixture was warmed to 30 °C and maintained at this temperature for 30 min. Upon completion of the reaction, the mixture was concentrated to 1.5 times the original volume and 10 ml of n-heptane was added slowly with continuous stirring. The resulting white solid was cooled to -20°C and stirred at this temperature for 1 hour. The suspension was filtered through a sintered glass funnel and the solid was washed three times with 3 ml of n-heptane. The solid was dried in air for 2 h to give a white acicular product in a yield of 700 mg in 87.4% yield. The structure of the product was confirmed by 1H NMR (DMSO-d6, 400 MHz): δ 1.39 (d, J = 7.5 Hz, 3H); 2.83 (s, 3H); 4.40 (q, J = 7.5 Hz, 1H).

1085528-19-3
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58311-53-8
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Yield: 87.4%

Reaction Conditions:

with thionyl chloride in dichloromethane at 20 - 30; for 0.583333 h;

Steps:

2 Preparation of (S)-3,4-dimethyl-1,3-oxazolidine-2,5-dione
Ex. 2 Preparation of (S)-3,4-dimethyl-1,3-oxazolidine-2,5-dione 1 g (6.2 mmol) of the product obtained previously was dissolved in 3 ml of CH₂Cl₂, stirred for 5 minutes at around 20° C., then treated with SOCl₂ (500 μl, 1.1 eq.). The reaction medium was then heated at around 30° C., and the heating was maintained for around 30 min. The reaction medium was then concentrated to around 1.5 volumes, and, still with stirring, 10 ml of n-heptane were added. The white mass thus obtained was then cooled to around -20° C., and stirred for 1 hour at this temperature. The suspension was then filtered through sintered glass, the solid was washed with 3 times 3 ml of n-heptane. After drying in air for 2 hours, the product (700 mg, 87.4%) was obtained in the form of white needles. Structural analyses: ¹H NMR (DMSO-d₆ at 400 MHz): 1.39 (d, J=7.5 Hz, 3H); 2.83 (s, 3H); 4.40 (q, J=7.5 Hz, 1H).

References:

SANOFI-AVENTIS US2010/113797, 2010, A1 Location in patent:Page/Page column 3-4