HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 6-tert-Butyl-4-(3-chloropropyl)-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-tert-Butyl-2H-1,4-benzoxazin-3(4H)-one | HCID 5129950 | — |
| Solvent | Ethylacetate heptane | HCID 21899848 | — |
| Product | 6-tert-Butyl-4-(3-chloropropyl)-4H-benzo[1,4]oxazin-3-one | HCID 68914429 | 49.3% |
Reaction Steps
6-tert-Butyl-4H-benzo[1,4]oxazin-3-one (81MF2248a) (2.07 g, 10.0 mmol), Cs2CO3 (4.88 g, 15.0 mmol) and 3-chloro-1-iodopropane (2.25 g, 11.0 mmol) were mixed according to GP6. CC (SiO2; Heptane/EtOAc 10:1-5) to give the title compound (81MF2248b) (1.39 g, 49%). 1H NMR (CDCl3) δ 7.12 (d, J=2.0 Hz, 1H), 7.03 (dd, J=8.4 Hz, J=2.0 1H), 6.92 (d, J=8.4 Hz, 1H), 4.54 (s, 2H), 4.14 (t, J=7.2 Hz, 2H), 3.65 (t, J=6.0 Hz, 2H), 2.21-2.14 (m, 2H), 1.32 (s, 9H); 13C NMR (CDCl3) δ 164.8, 146.4, 143.1, 127.9, 120.9, 116.7, 112.2, 67.8, 42.6, 38.9, 34.8, 31.6, 30.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576078B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-cd167ea49f4b450fb421e354cae72ce9 |
| Source note | uspto-grants-2009_08 |