Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzenamine, 4-(4-morpholinyl)- | HCID 75655 | — |
| Reactant | 1H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride | HCID 10986715 | — |
| Reactant | 5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic Acid | HCID 22054271 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22054216 | HCID 22054216 | 27% |
Reaction Steps
4-Morpholinoaniline (0.286 g, 1.60 mmol), triethylamine (0.162 g, 1.60 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.271 g, 1.60 mmol) were added to a methylene chloride solution (20 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.200 g, 0.535 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=1:2) and then recrystallized from ether to obtain the titled compound (0.077 g, 0.144 mmol, 27%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07064124B2 |
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| Source dataset | uspto-grants-2006_06 |
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| ORD ID | ord-374c397f802e4cf290bfc6ece8ff11ac |
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| Source note | uspto-grants-2006_06 |
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