HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoic acid, 3,5-dibromo- → 3,5-dibromo-N-cyclopropylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoic acid, 3,5-dibromo- | HCID 12063 | — |
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | — |
| Product | 3,5-dibromo-N-cyclopropylbenzamide | HCID 67062088 | — |
Reaction Steps
To a stirred solution of 3,5-dibromobenzoic acid (1 eq.) in DMF (0.15 M) was added HATU (1.3 eq.), cyclopropylamine (1.1 eq.) and Hunig's base (3 eq.). The resulting yellow mixture was stirred at RT for 18 h. The reaction was then quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Trituration of the crude product thus obtained in a mixture of ether and hexanes afforded the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08889714B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-3e4244c5b4c2486dbba4e4862f388986 |
| Source note | uspto-grants-2014_11 |