Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropylamine | HCID 6363 | — |
| Reactant | Epibromohydrin | HCID 18430 | — |
| Reactant | Maleate(2-) | HCID 5288227 | — |
| Reactant | HCID 86742417 | HCID 86742417 | — |
| Reactant | HCID 135856719 | HCID 135856719 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Diethylether ethylacetate | HCID 21584169 | — |
| Product | HCID 70416795 | HCID 70416795 | — |
Reaction Steps
A mixture of 3 g of 3-(4-epoxymethoxyphenyl)thieno[2,3-d]isoxazole (prepared from epibromohydrin and 3-(4-hydroxyphenyl)thieno[2,3-d]isoxazole in substantially the same manner as Example 5), 5 ml of absolute ethanol and 5 ml of isopropylamine was refluxed for three hours. The excess amine and ethanol were removed under a reduced pressure, leaving a residue. The crude product was extracted into 400 ml of ethyl acetate/ether (1:1) and shaken with ice-cold (10%) hydrochloric acid. The aqueous solution was separated and basified with concentrated NH3 to liberate the product. Extraction with ethyl acetate/ether (1:1) followed by washing and drying yielded a colorless solid weighing 2.8 g. The free base was converted to crystalline maleate in ethyl acetate/ether and recrystallized from methanol/ether to afford plates, m.p. 153°-155° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04769472 |
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| Source dataset | uspto-grants-1988_09 |
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| ORD ID | ord-47ef0b355b0e4fea8f5edd56c69a2ef4 |
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| Source note | uspto-grants-1988_09 |
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