Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | N,N-Dimethylaminoethyl chloride hydrochloride | HCID 11636816 | — |
| Reactant | HCID 53812483 | HCID 53812483 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 70343912 | HCID 70343912 | 59.1% |
Reaction Steps
2-(2,3-Dimethoxystyryl)-4,5,6,7-tetrahydrothiazolo[5,4-b]pyridine (1.0 g, 3.3 mmole) and powdery potassium carbonate (1.37 g, 9.92 mmole) were suspended in dimethylformamide (20 ml). To the suspension was added N,N-dimethylaminoethyl chloride hydrochloride (0.57 g, 3.97 mmole) and the mixture was heated with stirring at 90° C. for 4 hours. Water was added to the mixture and an organic substance was extracted with a chloroform-methanol mixed solvent. The extract was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography. The resulting oily compound was neutralized with hydrochloric acid and recrystallized from diethyl ether-ethanol to obtain the title compound (870 mg, yield: 54.4%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05153201 |
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| Source dataset | uspto-grants-1992_10 |
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| ORD ID | ord-8a495654e7e648dcb172bdb84287ed10 |
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| Source note | uspto-grants-1992_10 |
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