HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-(4-Amino-phenylsulfanyl)-N-(4-bromo-phenyl)-3-nitro-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Aminothiophenol | HCID 14510 | — |
| Reactant | N-(4-bromophenyl)-4-chloro-3-nitrobenzamide | HCID 1068537 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(4-Amino-phenylsulfanyl)-N-(4-bromo-phenyl)-3-nitro-benzamide | HCID 67040850 | 96% |
Reaction Steps
A solution of the product from Example 49A (3.0 g, 8.44 mmol), 4-aminothiophenol (1.06 g, 8.44 mmol) and cesium carbonate (5.5 g, 17.0 mmol) in N,N-dimethylformamide (15 mL) was heated to 90° C. for 4 hours. After cooling to room temperature the mixture was poured into ice water (100 mL) and the resultant solution acidified to pH 5 with 1N aqueous hydrochloric acid. The solution was then extracted with ethyl acetate (3×50 mL), the combined extracts dried over sodium sulfate, filtered and concentrated under vacuum to provide the title compound as an orange solid (3.6 g, 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08236950B2 |
| Source dataset | uspto-grants-2012_08 |
| ORD ID | ord-3f5ce05851f24513a0887fa2e1347e77 |
| Source note | uspto-grants-2012_08 |