HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → N-(2-Amino-5-chloro-phenyl)-5-bromo-2-fluoro-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Chloro-1,2-diaminobenzene | HCID 7263 | — |
| Reactant | 5-Bromo-2-fluorobenzoic acid | HCID 2736315 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(2-Amino-5-chloro-phenyl)-5-bromo-2-fluoro-benzamide | HCID 24699699 | 52% |
Reaction Steps
Method 7—Step a A mixture of 5-Bromo-2-fluoro-benzoic acid (3.00 g, 13.70 mmol), 4-chloro-benzene-1,2-diamine (2.42 g, 16.99 mmol), HATU (5.47 g, 14.38 mmol) and TEA (1.91 mL, 13.83 mmol) in dichloromethane (70 mL) and DMF (16 mL) was stirred at room temperature overnight, then water was added (80 mL) and left standing at room temperature overnight. The organic layer was divided and solvent removed under reduced pressure and the crude oil obtained was crystallized from the mixture of solvents dichloromethane:cyclohexane/3:1 (30 mL) to afford 2.19 g of the title compound (52%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08835648B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-b4ce010ef34c425eb8d782dbd571233d |
| Source note | uspto-grants-2014_09 |