Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylamine | HCID 1146 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | cis-Pent-2-ene-1-ol | HCID 5364919 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 86749996 | HCID 86749996 | 83.3% |
Reaction Steps
Z-2-Penten-1-ol (5.0 g, 58.1 mmol), trimethylamine (6.45 g, 63.9 mmol), methanesulfonylchloride (7.0 g, 61.1 mmol) and ether (30 ml) were allowed to react at ambient temperature for 1 hour. After the completion of the reaction, the insoluble matter was removed and washed with water. The washed substance was dried over sodium sulfate. The solvent was distilled off to obtain 7.95 g of Z-1-mesyloxy-2-pentene as pale yellow oily material (83.4%). This material was added to a mixture of 3,8-dimethyl-5-hydroxycarbostyril (7.0 g, 37.0 mmol), potassium carbonate (10.2 g, 74.0 mmol) and dimethylformamide (210 ml), and allowed to react at 70° C. for 1 hour. The reaction mixture was condensed under reduced pressure, and the residue was poured into water to obtain 7.36 g of the title compound as a brown solid (77.3%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05576324 |
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| Source dataset | uspto-grants-1996_11 |
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| ORD ID | ord-9333727f4f52455d9e0b365f6597994b |
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| Source note | uspto-grants-1996_11 |
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