HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 4-(3-Chloropropyl)-6-methoxy-4H-benzo[1,4]oxazin-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Chloro-3-iodopropane | HCID 81363 | — |
| Reactant | 6-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one | HCID 13204952 | — |
| Solvent | Ethylacetate heptane | HCID 21899848 | — |
| Product | 4-(3-Chloropropyl)-6-methoxy-4H-benzo[1,4]oxazin-3-one | HCID 68891997 | 42.1% |
Reaction Steps
6-Methoxy-4H-benzo[1,4]oxazin-3-one (81MF2249a) (0.212 g, 1.18 mmol), Cs2CO3 (0.578 g, 1.77 mmol) and 3-chloro-1-iodopropane (0.265 g, 1.3 mmol) were mixed according to GP5. CC (SiO2; Heptane/EtOAc 10:1-2) gave the title compound (81MF2249b) (0.127 g, 42%). 1H NMR (CDCl3) δ 6.88 (d, J=8.8 Hz, 1H), 6.62 (d, J=2.8 Hz, 1H), 6.50 (dd, J=2.8 Hz, J=8.8 Hz, 1H), 4.50 (s, 2H), 4.05-4.01 (m, 2H), 3.76 (s, 3H), 3.59 (t, J=6.2 Hz, 2H), 2.16-2.09 (m, 2H); 13C NMR (CDCl3) δ 164.8, 155.5, 139.3, 129.2, 117.4, 107.8, 101.9, 67.8, 55.8, 42.4, 38.9, 30.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680115B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-85a24651409140fbbbe299d640d5e4eb |
| Source note | uspto-grants-2014_03 |