HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → N-[5-bromo-3-methoxy-2-(2-methoxy-ethylamino)-phenyl]-4-isopropyl-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 4-Isopropylbenzoic Acid | HCID 10820 | — |
| Reactant | 5-bromo-3-methoxy-2-N-(2-methoxyethyl)benzene-1,2-diamine | HCID 57772082 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-[5-bromo-3-methoxy-2-(2-methoxy-ethylamino)-phenyl]-4-isopropyl-benzamide | HCID 57771993 | 98.6% |
Reaction Steps
A solution of 4.95 g (18 mmol) 5-bromo-3-methoxy-N*2*-(2-methoxy-ethyl)-benzene-1,2-diamine, 5.15 g (27 mmol) EDC, 3.3 g (27 mmol) 4-dimethylamino-pyridine and 2.94 g (18 mmol) 4-isopropyl benzoic acid in 150 ml dichloromethane is stirred at room temperature for 14 h. After that 400 ml EtOAc are added and the organic phase washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 7.48 g of the title compound as a reddish oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08030497B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-b101d0aac73548dfa072a1016acdd708 |
| Source note | uspto-grants-2011_10 |