(S)-(+)-Glycidyl phthalimide
(S)-(+)-Glycidyl Phthalimide
CAS: 161596-47-0
Molecular Formula: C11H9NO3
(S)-(+)-Glycidyl phthalimide - Names and Identifiers
(S)-(+)-Glycidyl phthalimide - Physico-chemical Properties
| Molecular Formula | C11H9NO3 |
| Molar Mass | 203.19 |
| Density | 1.446±0.06 g/cm3(Predicted) |
| Melting Point | 102 °C |
| Boling Point | 347.4±15.0 °C(Predicted) |
| Flash Point | 163.9°C |
| Solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| Vapor Presure | 0.001-2.17Pa at 25-90.25℃ |
| Appearance | White powder |
| Color | White |
| pKa | -2.24±0.20(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 10 ° (C=2.2, CHCl3) |
| MDL | MFCD04973350 |
(S)-(+)-Glycidyl phthalimide - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 41 - Risk of serious damage to eyes |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. |
| WGK Germany | 2 |
| HS Code | 29252900 |
(S)-(+)-Glycidyl phthalimide - Reference Information
| LogP | 1.2 at 40℃ |
| application | (S)-N-glycidyl phthalimide is also called S-glycidyl phthalimide. (S)-N-glycidyl phthalimide is an important intermediate for the preparation of rivaroxaban, the new antibiotic linezolid, antifungal thioxazolidinone, and oxazolidindione. (S)-N-glycidyl phthalimide is an organic amine compound and can be used as a pharmaceutical intermediate. It is an o-benzene diimide derivative used to prepare the antibiotic lineazole intermediate. |
| preparation | step 1. the preparation of N-(S-2, 2-dimethyl-1, 3-dioxolan-4-) methylphthalimide into a 1-liter four-mouth flask connected with stirring, thermometer and condenser tube, adding 250g of N,N-dimethylformamide (DMF), 37.0 grams (0.20 moles) of potassium phthalamide, 33.3 grams (0.22 moles) of R-2, 2-dimethyl-4-chloromethyl-1, 3-dioxolane, 0.5 grams of potassium iodide, heat, and keep the internal temperature between 80-85 ℃ and stir for 4 hours. Cool to 20 ℃, filter, wash the filter cake with 50g DMF, and combine the filtrate. DMF was recovered by vacuum distillation, and the remainder was recrystallized with 80g of methyl tert-butyl ether to obtain 49.7g of N-(S-2, 2-dimethyl-1, 3-dioxolan-4-) methyl phthalimide with 95.3% yield and 99.7% HPLC purity. Step 2. the preparation of S-glycidyl phthalimide into a 500 ml four-mouth bottle with stirring and thermometer, add 200g of 1,2-dichloroethane and 26.5g (0.10 mol) N-(S-2, 2-dimethyl-1, 3-dioxolan-4-) methylphthalimide, 25g of 40% hydrobromic acid, stir and react at 10-15 ℃ for 4 hours. Stratified, the water layer was extracted with 1, 2-dichloroethane 3 times, 20 grams each time, and the organic phase was combined, and the organic phase was transferred to the constant pressure liquid funnel. In another flask, 30g (0.15 mol) of 27% sodium methoxide methanol solution was added, the organic phase was added dropwise between 0-5 ℃, the dropwise after dropping, and the reaction was stirred at 10-15 ℃ for 3 hours. 200g of ice water was added, stratified, the water layer was extracted twice with 1, 2-dichloroethane, 20g each time, the organic phase was combined, 1, 2-dichloroethane was recovered by distillation, and the remainder was recrystallized with 50g of methyl tert-butyl ether to obtain 19.0g of S-glycidyl phthalimide with 93.6% yield and 99.9% HPLC purity. |
| use | rivaroxaban intermediate |
Last Update：2024-04-10 22:29:15
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