HuagongsheHuagongshe Chemistry Print Report · For research reference only
Stannous Chloride → Benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Stannous Chloride | HCID 24479 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 3-Fluoro-4-nitrobenzoic acid | HCID 230653 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Benzamide | HCID 2331 | — |
Reaction Steps
In one embodiment, intermediate [1C] is prepared according to Scheme 5A. In this route, 3-fluoro-4-nitro benzoic acid [Q1] is converted to corresponding amide [R1] using R7R8NH, EDCI.HCl, HOBt, TEA, and DMF at about rt for about 10 h. Amide [R1] is then reduced using SnCl2 in EtOH at reflux for about 3-4 h to provide benzamide [S1]. Benzamide [S1] is then converted to urea [T1] using 4-bromophenylisocyanate in the presence of TEA and DCM at about rt. Conversion of urea [T1] to intermediate [1C] is accomplished using Pd(dppf)Cl2.DCM, bis(pinacolato)diboron, KOAc, and 1,4-dioxane, at about 110° C. for about 10 h.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115092B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-c2249316971948008cbd65876b78037b |
| Source note | uspto-grants-2015_08 |