HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylcarbamoyl Chloride → 5-(2,5-Dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazole-3-carboxylic acid dimethylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylcarbamoyl Chloride | HCID 6598 | — |
| Reactant | Hexane | HCID 8058 | — |
| Reactant | 3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole | HCID 13248995 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-(2,5-Dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazole-3-carboxylic acid dimethylamide | HCID 59394761 | — |
Reaction Steps
To a solution of 3-(2,5-dimethyl-pyrrol-1-yl)-1-methyl-1H-pyrazole (2.0 g, 11.4 mmol) in THF (100 mL) at −78° C., 2.5M nBuLi in Hexane (5.5 mL, 13.7 mmol) is added. After stirring for 1.5 hour dimethylcarbamyl chloride (1.26 mL, 13.7 mmol) is added. After 10 min the ice bath is removed and the reaction allowed to reach room temperature and stir at room temperature for 2 hour before being poured into water, separated, and the water layer extracted with DCM. The organic layers are combined and concentrated. The residue is purified by FCC to give the title compound. MS (ESI) m/z 247.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08492393B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-29a32ae50fac41d5a944c716654b30c7 |
| Source note | uspto-grants-2013_07 |