HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → 3-(2-Oxazolyl)-4-chloroaniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sodium Dithionite | HCID 24489 | — |
| Reactant | 4-Chloro-3-nitrobenzoyl chloride | HCID 123477 | — |
| Reactant | 2-(2-Chloro-5-nitrophenyl)oxazole | HCID 19077609 | — |
| Reactant | HCID 178418936 | HCID 178418936 | — |
| Solvent | Sulfolane | HCID 31347 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | 3-(2-Oxazolyl)-4-chloroaniline | HCID 19077594 | — |
Reaction Steps
Following the procedure described in part E of Example 1 (R), (S)-α-[[[-((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 3-(2-oxazolyl)-4-chloroaniline to generate the title compound. The 3-(2-oxazolyl)-4-chloroaniline was prepared by treating commercial 4-chloro-3-nitrobenzoyl chloride sequentially with 1,2,3-triazole at 140° C. in sulfolane containing K2CO3 to generate 4-chloro-3-(2-oxazolyl)nitrobenzene which was reduced to the desired aniline with Na2S2O4 in THF/H2O at 90° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05770615 |
| Source dataset | uspto-grants-1998_06 |
| ORD ID | ord-f1feceba5cad4f4d8f6f28f5d2598196 |
| Source note | uspto-grants-1998_06 |