HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → N'-(3-chloro-4-(2-oxo-3-oxazolidinyl)phenyl)-N-methyl-N-(2-propenyloxy)urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Phosgene | HCID 6371 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Isocyanate | HCID 105034 | — |
| Reactant | 3-(2-Chloro-4-nitrophenyl)-2-oxazolidinone | HCID 23337318 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Nickel | HCID 935 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N'-(3-chloro-4-(2-oxo-3-oxazolidinyl)phenyl)-N-methyl-N-(2-propenyloxy)urea | HCID 23337321 | — |
Reaction Steps
4.8 g of 1B was reduced with hydrogen in a Parr shaker (Raney nickel catalyst, tetrahydrofuran solvent, 50 p.s.i.g. hydrogen). A solution of the resulting aniline in ethyl acetate was treated with an excess of phosgene (5 hours at reflux). A solution of the resulting isocyanate in tetrahydrofuran was treated with 3.5 g of 3C (12 hours, room temperature). The resulting crude product was purified by silica gel chromatography to give 3, as a white solid, mp: 133°-135° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04226612 |
| Source dataset | uspto-grants-1980_10 |
| ORD ID | ord-758e19832e8b46fc980e992dac68d235 |
| Source note | uspto-grants-1980_10 |