| Identification | More | [Name]
(S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE | [CAS]
171877-39-7 | [Synonyms]
4-BENZYL-THIAZOLIDIN-2-ONE
(S)-4-Benzyl-2-thiazolidinethione
(S)-4-BENZYL-THIAZOLIDINE-2-THIONE
(S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE
(4S)-4-Benzyl-1,3-thiazolidine-2-thione
(S)-(-)-BENZYL-1,3-THIAZOLIDINE-2-THIONE
(S)-4-Benzylthiazolidine-2-thione,99%e.e.
(S)-4-Benzylthiazolidine-2-thione, ee: 99%
2-Thiazolidinethione, 4-(phenylmethyl)-, (4S)-
(S)-4-Benzylthiazolidine-2-thione >=95.0% (GC)
(4S)-4-Benzyl-2-thioxo-1,3-thiazolidine, (4S)-4-(Phenylmethyl)-2-thioxo-1,3-thiazolidine | [Molecular Formula]
C10H11NS2 | [MDL Number]
MFCD06658216 | [Molecular Weight]
209.33 | [MOL File]
171877-39-7.mol |
| Chemical Properties | Back Directory | [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 | [form ]
solid | [pka]
13.01±0.40(Predicted) | [color ]
Off-white | [Optical Rotation]
[α]20/D -122±5°, c = 1% in chloroform | [CAS DataBase Reference]
171877-39-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10-23 | [Hazard Note ]
Irritant | [HS Code ]
29341000 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white crystalline | [Uses]
| [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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