HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1972254Generated: October 30, 2026
1,2-Diaminocyclohexane → 3-[4-(4-Chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one
https://huagongshe.com/reaction/1972254
Participants
| Role | Name | HCID | Charge |
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| Reactant | 1,2-Diaminocyclohexane | HCID 4610 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1-Chloro-4-(4-iodophenoxy)benzene | HCID 19351990 | — |
| Reactant | benzyl N-[2-hydroxy-1-(3-methoxyphenyl)ethyl]carbamate | HCID 68702649 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-[4-(4-Chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one | HCID 68706069 | 76.8% |
Reaction Steps
To a dry round bottom flask is added [2-hydroxy-1-(3-methoxy-phenyl)ethyl]-carbamic acid benzyl ester (300 mg, 1 mmol), 1-(4-chlorophenoxy)-4-iodobenzene (330 mg, 1 mmol), K3PO4 (210 mg), 1,2-cyclohexanediamine (15 μL) and CuI (20 mg), and DMF (5 mL). The mixture is evacuated and back-filled with nitrogen three times. The reaction mixture is heated to 110° C. for 7 h. The reaction is then cooled to room temperature, diluted with EtOAc (50 mL), washed with 1N HCl, and brine, subsequently dried over MgSO4, filtered, and concentrated to give the crude product, which is purified by flash chromatography on silica gel (EtOAc/Hex: 1/2) to provide 3-[4-(4-chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one (304 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08431607B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-cf706bf919a247b6a5484cd9716f50ea |
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| Source note | uspto-grants-2013_04 |
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