1-Methyl-2-thioxoimidazolidin-4-one CAS#: 29181-65-5; ChemWhat Code: 1384138
Identification
| Product Name | 1-Methyl-2-thioxoimidazolidin-4-one |
| IUPAC Name | 1-methyl-2-sulfanylideneimidazolidin-4-one |
| Molecular Structure |  |
| CAS Registry Number | 29181-65-5 |
| EINECS Number | No data available |
| MDL Number | MFCD24549243 |
| Beilstein Registry Number | No data available |
| Synonyms | 1-methyl-2-thioxoimidazolidin-4-one, 1-methyl-2-sulfanylideneimidazolidin-4-one, 1-methyl-2-thioxo-imidazolidin-4-one, 1-methyl-2-thiohydantoin, 1-methyl thiohydantoin, 1-Methyl-2-thioxo-imidazolidin-4-on, 1-methyl-2-thioxo-4-imidazolidinone CAS 29181-65-5 CAS N0: 29181-65-5 |
| Molecular Formula | C4H6N2OS |
| Molecular Weight | 130.168 |
| InChI | InChI=1S/C4H6N2OS/c1-6-2-3(7)5-4(6)8/h2H2,1H3,(H,5,7,8) |
| InChI Key | MOKGHQUWPQTSDM-UHFFFAOYSA-N |
| Canonical SMILES | CN1CC(=O)NC1=S |
| Patent Information |
| No data available |
Physical Data
| Appearance | Yellow-green solid |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Melting Point, °C | Solvent (Melting Point) |
| 222 – 224 | |
| 230 – 232 | |
| 227 – 229 | |
| 223 – 224.5 | |
| 224 – 226 | aq. ethanol |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz | Original Text (NMR Spectroscopy) |
| 1H | dimethylsulfoxide-d6 | 1H NMR (DMSO-d6): δ 11.67 (s, 1H); 4.27 (s, 2H); 3.23 (s, 3H); | ||
| 13C | dimethylsulfoxide-d6 | 13C NMR (DMSO-d6): δ 181.5, 172.1, 55.1, 32.7 | ||
| Chemical shifts | 1H | dimethylsulfoxide-d6 | ||
| Chemical shifts | 13C | dimethylsulfoxide-d6 | ||
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 300 | |
| Chemical shifts | 13C | dimethylsulfoxide-d6 | 75 | |
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 200 | |
| 1H | D2O | |||
| NMR |
| 1-Methyl-2-thioxoimidazolidin-4-one CAS#: 29181-65-5 NMR |  |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Comment (IR Spectroscopy) |
| Bands | KBr | |
| Bands | KBr | 1750 – 900 cm**(-1) |
| Description (Mass Spectrometry) |
| EI (Electron impact) |
| GCMS (Gas chromatography mass spectrometry), EI (Electron impact), Spectrum |
| EI (Electron impact), Spectrum |
| HRMS (High resolution mass spectrometry), Spectrum |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm |
| Absorption maxima | ethanol | 230, 265 |
| Absorption maxima | H2O | 230, 261 |
| Absorption maxima | aq. NaOH | 258 |
Route of Synthesis (ROS)
| Conditions | Yield |
| at 140℃; Experimental Procedure Example 83: (5Z)-2-(l,2-diazinan-l-yl)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-l- methyl-4,5-dihydro-lH-imidazol-4-; 3Et3NO EtOH Refluxo neA mixture of sarcosine (1.0 g, 11.2 mmol) and ammonium thiocyanate (2.56 g, 33.6 mmol) was heated at 140 0C overnight without stirring. After cooling to room temperature, diethyl ether (25 mL) was added to the solution, and the solid residue was triturated with water (100 mL). The solid product was recovered by filtration, washed with water (3 x 50 mL), ethanol (1 x 50 mL) and diethyl ether (1 x 50 mL), and dried in vacuo, affording l-methyl-2- thioxoimidazolidin-4-one (1.40 g, 96%). The product was used without further purification.A mixture of 1 -methyl-2-thioxoimidazolidin-4-one (1.40 g, 10.8 mmol), A- fluorosalicylaldehyde (1.51g, 10.8 mmol) and ammonium acetate (832 mg, 10.80 mmol) in acetic acid (75 mL) was stirred at reflux overnight. After cooling to room temperature, the solvent was evaporated. Water (50 mL) was then added to the residue. The mixture was extracted with EtOAc (1 x 50 mL). The organic phase was recovered and extracted with brine (3 x 5OmL), dried over MgSO4, filtered, evaporated, and dried in vacuo, affording the thiol dimer intermediate (872 mg, 32%). The product was used without further purification. To a mixture of thiol dimer (872 mg, 3.5 mmol) in absolute EtOH (25 mL) was added JV-JV-diisopropylethylamine (700 μL, 4.0 mmol) and iodomethane (435 μL, 7.0 mmol). The reaction mixture was stirred at room temperature overnight. The solid material was recovered by filtration, washed with EtOH (3 x 20 mL), diethyl ether (1 x 10 mL), and dried in vacuo, affording the methylated thiol. The product was used without further purification. To a mixture of methylated thiol intermediate (523 mg, 1.2 mmol) in absolute ethanol (10 mL) was added hexahydropyridazine dihydrochloride (509 mg, 8.0 mmol) and triethylamine (1.1 mL, 8.0 mmol). The reaction mixture was stirred at reflux overnight. After cooling to room temperature, the solid material was recovered by filtration and washed with EtOH (2 x 15 mL), diethyl ether (2 x 10 mL), and dried in vacuo, affording the final product (335 mg, 92%). 1H NMR (400 MHz, DMSO-J6) δ 1.61 (m, 2H), 1.74 (m, 2H), 2.92 (m, 2H), 3.52 (s, 3H), 3.65(m 2H), 5.29 (t, IH, J= 7.0 Hz), 6.48 (s, IH), 6.63 (m, 2H), 8.37 (t, IH, J= 7.0 Hz); M+ 360. | 96% |
| at 140℃; for 19h; Inert atmosphere; | 90% |
| at 140℃; for 12h; Cycloaddition; | 55% |
| at 140℃; for 6h; Inert atmosphere; Experimental Procedure The mixture of 2-alkylaminoacetic acid (0.1 mol) and NH4SCN (22.8g, 0.3 mol) was heated at 140°C for 6 hours. The dark red solution was cooled. The solid cake formed was crashed with spatula, washed with 40 ml of H20 and collected. The crystals were then washed successively with H20, 95% ethanol and hexane to give 7.5 g (65%) of light tan crystals after drying.[0126] l-Methyl-2-thioxo-imidazolidin-4-one (11a): mp 222-224°C, 45% yield, light tan crystals; 1H NMR (DMSO-d6): δ 11.67 (s, 1H); 4.27 (s, 2H); 3.23 (s, 3H); 13C NMR (DMSO-d6): δ 181.5, 172.1, 55.1, 32.7. MS (EI): m/z 130.0 [M]+. | 45% |
| at 140℃; Inert atmosphere; |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | No data available [Warning?Hazardous to the aquatic environment, long-term hazard] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | No data available (The corresponding statement to each P-code can be found at the GHS Classification page.) For more detailed information, please visit ECHA C&L website |
| Source: European Chemicals Agency (ECHA) License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. License URL: https://echa.europa.eu/web/guest/legal-notice Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446 Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database |
Other Data
| Transportation | No data available |
| Under the room temperature and away from light | |
| HS Code | No data available |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 130.17 |
| logP | -0.122 |
| HBA | 3 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 64.43 |
| Rotatable Bond (RotB) | 0 |
| Matching Veber Rules | 2 |
| Use Pattern |
| 1-Methyl-2-thioxoimidazolidin-4-one CAS#: 29181-65-5 is used as an anticancer drug intermediate. |
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