Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bromine | HCID 24408 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | 2-Amino-4-nitrobenzonitrile | HCID 11147897 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 57423043 | HCID 57423043 | 36% |
Reaction Steps
2-Amino-4-nitrobenzonitrile (1.6 g, 9.81 mmol) is presented as an initial charge in 30 mL of dioxane and is mixed at 10° C. with bromine (0.56 mL, 11 mmol). This is followed by stirring at 60° C. for 6 hours. After cooling to room temperature, the batch is added to dilute sodium thiosulphate solution. After extraction of dichloromethane, the combined organic phases are dried over sodium sulphate to leave, after removal of the solvent and chromatographic purification (silica gel, n-hexane/ethyl acetate: 0→100% ethyl acetate), the product in 36% yield (820 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07863283B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-b9a5937cd98e47a68b97f74cd27c51cb |
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| Source note | uspto-grants-2011_01 |
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