HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenol → n-Benzyl-1-methyl-4-nitro-3-phenoxy-1h-pyrazol-5-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenol | HCID 996 | — |
| Reactant | Carbonate Ion | HCID 19660 | — |
| Reactant | benzyl(5-bromo-4-nitro-2-propyl-2H-pyrazol-3-yl)amine | HCID 13007229 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | n-Benzyl-1-methyl-4-nitro-3-phenoxy-1h-pyrazol-5-amine | HCID 57957914 | — |
Reaction Steps
Treatment of 3,5-dibromo-4-nitro-1H-pyrazole 1 with MeI and NaH in DMF affords 3,5-dibromo-1-methyl-4-nitro-1H-pyrazole 2. Nucleophilic aromatic substitution of the compound 2 with benzylamine in DMSO produces benzyl-(5-bromo-2-methyl-4-nitro-2H-pyrazol-3-yl)-amine 3. Treatment of the compound 3 with phenol in the presence of copper (I) iodide and cecium carbonate in N-methylpyrrolidinone (NMP) under microwave irradiation provides N-benzyl-1-methyl-4-nitro-3-phenoxy-1H-pyrazol-5-amine 4 (Tetrahedron Lett, 2003, 44, 3445). Hydrogenation of the compound 4 with Pd/C at 60 psi hydrogen in ethanol affords 1-methyl-3-phenoxy-1H-pyrazole-4,5-diamine 5. II. Keratin Dyeing Composition Components
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07850742B2 |
| Source dataset | uspto-grants-2010_12 |
| ORD ID | ord-c202959e29b74a5aa414af910efce754 |
| Source note | uspto-grants-2010_12 |