| Identification | More | [Name]
((5-Thiazolyl)methyl)-(4-nitrophenyl)carbonate | [CAS]
144163-97-3 | [Synonyms]
((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate
carbonic acid 4-nitrophenyl 5-thiazolylmethyl ester
Thiazolylmethyl-4-nitrophenylcarbonate | [EINECS(EC#)]
680-587-3 | [Molecular Formula]
C11H8N2O5S | [MDL Number]
MFCD09750981 | [Molecular Weight]
280.26 | [MOL File]
144163-97-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale-Yellow Solid | [Melting point ]
65-67°C | [Boiling point ]
475.3±45.0 °C(Predicted) | [density ]
1.485 | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
Chloroform, Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
1.86±0.10(Predicted) | [color ]
Pale Yellow | [Usage]
Retinovir intermediate | [InChI]
InChI=1S/C11H8N2O5S/c14-11(17-6-10-5-12-7-19-10)18-9-3-1-8(2-4-9)13(15)16/h1-5,7H,6H2 | [InChIKey]
FTEKBGGQRNJIPQ-UHFFFAOYSA-N | [SMILES]
C(OCC1SC=NC=1)(=O)OC1=CC=C([N+]([O-])=O)C=C1 | [CAS DataBase Reference]
144163-97-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Pale-Yellow Solid | [Uses]
Retinovir intermediate | [Uses]
Retinovir intermediate. | [Synthesis]
General procedure for the synthesis of ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate (compound 9) from 5-hydroxymethylthiazole (compound 8, 17 mmol) and bis(p-nitrophenyl)carbonate (compound 7, 19 mmol): compound 7 was added to a dichloromethane (DCM, 40 mL) solution of compound 8, followed by triethylamine (26 mmol) . The reaction mixture was stirred at room temperature for 12 h. After completion of the reaction it was concentrated under reduced pressure. The concentrated mixture was diluted with ethyl acetate (EtOAc) and washed sequentially with saturated aqueous sodium carbonate (Na2CO3) solution, water and brine. After washing, the organic solvent was removed under reduced pressure. The residue was purified by fast column chromatography (silica gel as stationary phase, eluent ratio hexane/ethyl acetate=1/1) to give the final compound 9 (4.7 g). | [References]
[1] Patent: WO2008/10921, 2008, A2. Location in patent: Page/Page column 188-189
[2] Patent: US2010/256366, 2010, A1. Location in patent: Page/Page column 19
[3] Patent: EP2231628, 2015, B1. Location in patent: Paragraph 0878
[4] Patent: US2018/30043, 2018, A1. Location in patent: Paragraph 0163 |
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