HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → 5-(Hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Benzyl phenylcarbamate | HCID 319368 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (S)-(+)-Glycidyl butyrate | HCID 6999819 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Propan-2-one--water (1/1) | HCID 18366337 | — |
| Product | 5-(Hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-one | HCID 207132 | — |
Reaction Steps
In Scheme 4, aniline (62) and benzyl chloroformate (63) are reacted in the presence of NaHCO3 and acetone:water (2:1) to generate benzyl N-phenylcarbamate (64), which when reacted with Cs2CO3 and (S)-(+)-glycidyl butyrate (65), in DMF solution gives the 5-(hydroxymethyl)-3-phenyloxazolidin-2-one (66), which upon treatment with NaIO4, RuCl3, H2O generates (67).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08283346B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-f649fb888b69435e941e261e032bf054 |
| Source note | uspto-grants-2012_10 |