Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Veratroyl chloride | HCID 77070 | — |
| Reactant | HCID 23107570 | HCID 23107570 | — |
| Reactant | pyridine-4-thiol | HCID 178418431 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 23107819 | HCID 23107819 | 67% |
Reaction Steps
Subsequently, methyl 5-bromo-2-[3-(chloromethyl)benzoyl]aminobenzoate (1.5 g) was dissolved in anhydrous methylene chloride. Triethylamine (2.0 ml) and 4-mercaptopyridine (compound B′) (880 mg) were added to the solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over sodium sulfate, and was then concentrated. Diethyl ether was added to the residue for crystallization. The crystals were filtered through Kiriyama Rohto (21 mmφ) and were washed with diethyl ether to give methyl 5-bromo-2-(3-[(4-pyridylsulfanyl)methyl]benzoylamino)benzoate (1.20 g, yield 67%) as a useful intermediate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08134015B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-ab7c07bdbe4a4424991d77c59f404486 |
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| Source note | uspto-grants-2012_03 |
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