Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Dimethylamine | HCID 674 | — |
| Edukt | 2-Phthalimidoethanethiol | HCID 96248 | — |
| Edukt | 2,6-Bis(chloromethyl)pyridine | HCID 316654 | — |
| Edukt | Sodium Methoxide | HCID 10942334 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | HCID 20434281 | HCID 20434281 | — |
Reaktionsschritte
To a solution of N-(2-mercaptoethyl) phthalimide (28.8 g, 0.139 mol) in dry methanol (250 ml) is added sodium methoxide (7.5 g, 0.139 mol) with cooling and stirring. This mercaptide solution is added to 2,6-bis(chloromethyl)pyridine (24.5 g, 0.139 mol) in dry methanol (250 ml). The mixture is stirred at room temperature for 21/2 hours and is filtered to remove the precipitated solid. Then dimethylamine (6.9 g, 0.153 mol) in cold methanol (150 ml) is added to the filtrate and the mixture is stirred at room temperature overnight. The solvent is removed in vacuo leaving an amber gum. The gum is taken up in methylene chloride (200 ml) and is washed with aqueous sodium bicarbonate and with water. The methylene chloride layer is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. This gives 24.3 g of 6-dimethylaminomethyl-2-[(2-phthalimidoethyl)thiomethyl]pyridine as a crude amber gum.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US04490533 |
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| Quelldatensatz | uspto-grants-1984_12 |
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| ORD ID | ord-68ae5f5889ee49be83fb4a3600db0820 |
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| Quellennotiz | uspto-grants-1984_12 |
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