HuagongsheHuagongshe Chemistry Print Report · For research reference only
Iodine → N-(3-trifluoromethoxy-phenyl)-malonamic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Iodine | HCID 807 | — |
| Reactant | 3-(Trifluoromethoxy)aniline | HCID 73753 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | Benzyl malonate | HCID 22247814 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | N-(3-trifluoromethoxy-phenyl)-malonamic acid benzyl ester | HCID 69284656 | 83.4% |
Reaction Steps
Preparation I2, Step 1: A solution of mono-benzyl malonate (1.1 g, 5.6 mmol) in 3:1 CH2Cl2/DMF (28 mL) was treated sequentially with N,N-diisopropylethylamine (2.5 mL, 14.0 mmol), meta-trifluoromethoxy-phenylamine (0.75 mL, 5.6 mmol), and HATU (2.6 g, 6.7 mmol). The mixture was stirred for 12 h at RT, concentrated in vacuo, and partitioned between EtOAc and sat. NH4Cl. The aqueous phase was extracted with EtOAc (1×). The combined organic extracts were washed with sat. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography to provide N-(3-trifluoromethoxy-phenyl)-malonamic acid benzyl ester as an oil (1.65 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07378409B2 |
| Source dataset | uspto-grants-2008_05 |
| ORD ID | ord-cf5ec41b3c0c4d58ae8cb32e6109bb1c |
| Source note | uspto-grants-2008_05 |