Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Benzoic Acid | HCID 243 | — |
| Reactant | 4-Bromoaniline | HCID 7807 | — |
| Reactant | 2-Methyl-3-butyn-2-ol | HCID 8258 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 22000958 | HCID 22000958 | — |
Reaction Steps
A mixture of 4-bromoaniline (1.72 g, 10 mmol), benzaldehyde (0.27 g free of benzoic acid, 2.5 mmol), benzoic acid (20 mg, 0.16 mmol), PdCl2 (2 mg) and triethylamine (3.5 g) was deaerated by bubbling nitrogen and then heated to reflux for 30 min. The reaction mixture was cooled to 50° C. and treated with triphenylphosphine (73 mg in 0.5 g of TEA) followed by 2-methyl-3-butyn-2-ol (1.1 g, 13 mmol) and then CuI (20 mg in 1 g TEA). This mixture was heated at reflux for 12 hr. Thin layer chromatography showed the reaction to form 3-aminophenylacetylene dimethylcarbinol, in mixture with N-benzylidene 3-aminophenylacetylene dimethylcarbinol, to be complete.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06225499B1 |
|---|
| Source dataset | uspto-grants-2001_05 |
|---|
| ORD ID | ord-26deebafc5b04a20a4d34d99c554001e |
|---|
| Source note | uspto-grants-2001_05 |
|---|
