HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 6-Chloro-4-(3-chloropropyl)-7-nitro-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-Chloro-7-nitro-2H-1,4-benzoxazin-3(4H)-one | HCID 3305696 | — |
| Solvent | Ethylacetate heptane | HCID 21899848 | — |
| Product | 6-Chloro-4-(3-chloropropyl)-7-nitro-4H-benzo[1,4]oxazin-3-one | HCID 68910914 | 40.3% |
Reaction Steps
Crude 6-Chloro-7-nitro-4H-benzo[1,4]oxazin-3-one (81MF2253a) (2.60 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) gave the title compound (81MF2253b) (1.23 g, 36%). 1H NMR (CDCl3) δ 7.66 (s, 1H), 7.20 (s, 1H), 4.70 (s, 2H), 4.12 (t, J=7.6 Hz, 2H), 3.67-3.59 (m, 2H), 2.21-2.13 (m, 2H); 13C NMR (CDCl3) δ 163.6, 143.5, 133.3, 133.2, 122.4, 117.2, 115.2, 67.4, 42.1, 39.6, 29.8.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680115B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-5ebb5b1933ab4a28835e0e178040525f |
| Source note | uspto-grants-2014_03 |