HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 4-Hydroxy-N-methoxy-N-methylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 4-Hydroxybenzoic Acid | HCID 135 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-Hydroxy-N-methoxy-N-methylbenzamide | HCID 11389757 | — |
Reaction Steps
A mixture of 4-hydroxybenzoic acid (20.29 g, 147 mmol), N,O-dimethylhydroxylamine hydrochloride (21.49 g, 220 mmol), N-ethyl-N-isopropylpropan-2-amine (77 mL, 441 mmol), hobt (22.50 g, 147 mmol), and EDC (33.8 g, 176 mmol) in DMF (100 mL) was stirred at RT in 24 h. H2O was added, extracted with ether (3×), dried over MgSO4, concentrated, and purified by ISCO (40% EtOAc/Hexanes) to give the titled compound. MS [M+1]: 182.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08329700B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-27fb31cf2cca48c7a4a891a5c951c378 |
| Source note | uspto-grants-2012_12 |