Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 6-Aminohexanoic Acid | HCID 564 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Ethanesulfonyl chloride | HCID 11667 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 16781337 | HCID 16781337 | 40% |
Reaction Steps
A solution of ethanesulfonyl chloride (3.9 ml, 41.1 mmol) in dioxane (10 ml) was added to a solution of 6-aminohexanoic acid (2 g, 15.2 mmol) in 1N NaOH (56 ml) and dioxane (10 ml), while stirring at 0° C.-5° C. The pH of the reaction mixture was adjusted to 8-9 by addition of 25% sodium hydroxide solution. The mixture was allowed to warm to room temperature and stirred for 30 minutes. Further 25% NaOH solution was added to adjust the pH to about 11. After 3.5 h 1N hydrochloric acid (15 ml) and ethyl acetate (60 ml) were added. The organic layer was dried over sodium sulfate and concentrated. The residue was triturated with a mixture of diethyl ether (5 ml) and hexane (15 ml). The solid was collected by filtration and dried affording 1.3 g of the title compound (40% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546608B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-16acb1dc1d2b4347915bee2562cbfaec |
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| Source note | uspto-grants-2013_10 |
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