Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Bromoaniline | HCID 7807 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 2,6-Dichlorobenzothiazole | HCID 77176 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | HCID 7147097 | HCID 7147097 | — |
Reaction Steps
A mixture of 2,6-dichlorobenzothiazole (0.71 g, 3.5 mmol) and 4-bromoaniline (0.61 g, 3.5 mmol) in n-butanol (6 mL) was heated at 60-70° C. under nitrogen to obtain a solution, to which 4 M HCl in dioxane (0.43 mL, 1.73 mmol) was then slowly added dropwise. The reaction mixture was then heated at 90° C. for 18 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure. The resulting solid was triturated with ethanol and collected by filtration. This yielded 1.09 g (93%) of the title compound. LC/MS m/z 339 (MH+); retention time 3.98 min. 1H NMR (CD3OD) δ 7.31 (d, 1H), 7.42-7.58 (m, 5H), 7.61 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07759376B2 |
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| Source dataset | uspto-grants-2010_07 |
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| ORD ID | ord-ca305b51c29f466bb36291b0d4ac80aa |
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| Source note | uspto-grants-2010_07 |
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