Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,6-Dibromohexane | HCID 12368 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-(4-Acetylamino-3-fluorophenyl)-5-amino-6,8-difluoro-4H-1-benzopyran-4-one | HCID 19434907 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 19434847 | HCID 19434847 | 83% |
Reaction Steps
5.00 g (14.4 mmol) of Compound 27 obtained in Example 27 was dissolved in 150 ml of dimethylformamide under argon atmosphere, 10.9 ml of 1,6-dibromohexane and 575 mg of sodium hydride (60% oil dispersion) were added under ice-cooling and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:acetone=20:1) to give 6.11 g (83%) of 2-[4-[N-acetyl-N-(6-bromohexyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05539112 |
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| Source dataset | uspto-grants-1996_07 |
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| ORD ID | ord-96ab6806060e4bb18d6837a501f05c34 |
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| Source note | uspto-grants-1996_07 |
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