Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 2-Methyl-3-furoic acid | HCID 244756 | — |
| Reactant | 1,1,3-Trimethylindan-4-amine | HCID 11217541 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 14054112 | HCID 14054112 | 65% |
Reaction Steps
A mixture of 1.5 g (11.9 mmols) of 2-methyl-3furan carboxylic acid with 3 ml of thionyl chloride was refluxed for 1 hour. The reaction solution was distilled under reduced pressure to remove excess thionyl chloride. The obtained residue was cooled and 20 ml of ethyl acetate, 2 g (19.8 mmols) of triethylamine, and 1.8 g (10.3 mmols) of 1,1,3-trimethylindane-4-amine were added thereto. The resultant mixture was stirred at room temperature for 2 hours. The reaction solution was sequentially washed with water and brine. The organic layer consequently separated was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was purified by being recrystallized with ethyl acetate/n-hexane, to obtain 1.8 g of white crystals (Compound No. 17 shown in Table 6). The yield was 65%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04956375 |
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| Source dataset | uspto-grants-1990_09 |
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| ORD ID | ord-0db9be5c1470445cad7cb70be8e860da |
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| Source note | uspto-grants-1990_09 |
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