Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 18376742 | HCID 18376742 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 18376807 | HCID 18376807 | 93% |
Reaction Steps
Into a solution of N-(5-chloropyridin-2-yl)-2-nitro-3,5-dichlorobenzamide (4.0 g, 12 mmol) in dimethyl sulfoxide (60 mL) was bubbled an excess of dimethyl amine gas. The mixture was sealed in a pressure tube and heated at 50° C. After 3 hours, the mixture was cooled to ambient temperature, then poured into water, and extracted with methylene chloride. The combined organic extracts were dried over MgSO4, and concentrated in vacuo to afford 3.8 g (93% yield) of N-(5-chloropyridin-2-yl)-2-nitro-3-dimethylamino-5-chlorobenzamide; NMR (CDCl3) 9.6 (s, 1), 8.2 (d, 1), 7.8 (d, 1), 7.7 (dd, 1), 7.1 (d, 1), 6.9 (d, 1), 2.8 (s, 6) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06380221B1 |
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| Source dataset | uspto-grants-2002_04 |
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| ORD ID | ord-2320183d2eb0407f84f6af52b16e67b7 |
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| Source note | uspto-grants-2002_04 |
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