Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanethiol | HCID 878 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | 1-Benzyl-2,5-dihydropyrrole | HCID 561506 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | HCID 12044052 | HCID 12044052 | 64% |
Reaction Steps
To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 12.0 g (0.12 mol) of 98% sulfuric acid, 15.0 g of water, and 60.0 g of acetone in a quartz round flask reactor, 45.6 g (0.20 mol) of (NH4)2S2O8 (ammonium peroxydisulfate produced by Mitsubishi Gas Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 5 days at room temperature with irradiation by 500W Xe lamps (UXL-500D xenon lamp produced by Ushio). 14.4 g (0.3 mol) of methanethiol (produced by produced by Aldrich Chemical Co., Inc.) was continuously added to the reaction mixture and stirred for 5 hours under reflux. After completion, acetone and excess diethylamine were evaporated under reduced pressure, and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 14.3 g of 1-benzyl-4-methylthio-3-pyrrolidinol (yield 63.9%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06479668B1 |
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| Source dataset | uspto-grants-2002_11 |
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| ORD ID | ord-9ba671b317a84cd5bb67c7dc1dee1543 |
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| Source note | uspto-grants-2002_11 |
|---|
