(S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE Chemical Properties

Melting point:

93-94℃

Boiling point:

328.4±25.0 °C(Predicted)

Density 

1.27±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

13.01±0.40(Predicted)

form 

solid

color 

Off-white

optical activity

[α]20/D -122±5°, c = 1% in chloroform

InChI

1S/C10H11NS2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m0/s1

InChIKey

SLDUGQISGRPGAW-VIFPVBQESA-N

SMILES

S=C1N[C@H](CS1)Cc2ccccc2

CAS DataBase Reference

171877-39-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-23

Hazard Note 

Irritant

HS Code 

29341000

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

(S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE Usage And Synthesis

Chemical Properties

Off-white crystalline

Uses

Evans-Type Oxazolidinethione And Thiazolidinethione Auxiliaries

Synthesis

The general procedure for the synthesis of S-4-benzylthiazolidine-2-thione from the compound (CAS: 131744-19-9) is as follows: the crude oxazolidinethione was dissolved in carbon disulfide (CS2, 364.0 mL, 5.95 mol), followed by the addition of 1N aqueous potassium hydroxide (KOH) solution (5.95 L). The reaction mixture was heated to 100 °C and stirred at this temperature for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane (CH2Cl2, 3 x 3 L). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and rinsed through a silica gel plug (800 g) with a 1:1 solvent mixture of hexane/ethyl acetate (EtOAc, 2 L). Subsequently, the crude product was concentrated by rotary evaporation. The crude product was further purified by fast chromatography using a gradient elution from hexane to 1:1 hexane/ethyl acetate to give S-4-benzylthiazoline-2-thione (S2, 201.5 g, 81% yield). Supporting information S2: Thin-layer chromatography (TLC, 1:1 hexane/EtOAc): Rf = 0.31; 1H NMR (CDCl3, 500 MHz) δ 8.36 (broad single peak, 1H), 7.32 (multiple peaks, 2H), 7.26 (multiple peaks, 1H), 7.18 (multiple peaks, 2H), 4.46 (double double peaks, J = 7.5, 15.0 Hz, 1H), 3.50 (double triple peak, J = 7.9, 11.5 Hz, 1H), 3.25 (double triple peak, J = 7.2, 11.5 Hz, 1H), 3.04 (multiple peaks, 1H), 2.93 (multiple peaks, 1H); 13C NMR (CDCl3, 125 MHz) δ 200.5, 135.7, 129.0, 128.9, 127.2, 65.1, 39.7, 37.8; Fourier Transform Infrared Spectroscopy (FTIR, thin film) vmax 3154, 1602, 1495, 1437, 1327, 1297, 1279, 1233, 1204, 1040, 1008, 957, 743 cm-1; High Resolution Electrospray Ionization Mass Spectrometry (HR- ESI-MS) m/z calculated value for C10H11NS2 [M]+: 209.0333, measured value 209.0342.

References

[1] Organic Letters, 2012, vol. 14, # 21, p. 5396 - 5399
[2] Patent: WO2013/148324, 2013, A1. Location in patent: Paragraph 0158-0159
[3] Journal of Organic Chemistry, 1995, vol. 60, # 20, p. 6604 - 6607
[4] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 14, p. 2139 - 2145

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