Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | 1-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-one | HCID 521105 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | HCID 60207311 | HCID 60207311 | 42.7% |
Reaction Steps
To a solution of 1-(5-chloro-4-nitro-2-thienyl)ethanone (1 g, 4.9 mmol) in isopropanol (20 mL), was added dimethylamine (0.55 g, 6.8 mmol) and paraformaldehyde (0.22 g, 7.3 mmol) and concentrated hydrochloric acid (0.2 mL). The resulting reaction mixture was heated at 80° C. for 18 hours. After this time, the reaction mixture was cooled to 0° C. and stirred at 0° C. for 1 hour. A pale yellow precipitate formed and collected by filtration to afford the corresponding hydrochloride salt of the title product (0.55 g, 38% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.39 (1H, m), 8.69 (1H, s), 3.68 (2H, m), 3.38 (2H, m), 2.80 (6H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680139B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-f608357ec7fc4e8da758d4e727def918 |
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| Source note | uspto-grants-2014_03 |
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