Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Thiophosgene | HCID 10040 | — |
| Reactant | HCID 28412179 | HCID 28412179 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 85951409 | HCID 85951409 | 77.2% |
Reaction Steps
5-(3-Fluorophenoxy)-2-pyridinamine (210 mg, 1 mmol) was dissolved in dry degassed methylene chloride (5 ml) and thiophosgene (0.11 ml, 1.3 mmol) was added through syringe during 5-10 min to the stirred solution. Pyridine (0.18 ml, 2 mmol) was added to the reaction mixture right after the addition of thiophosgene and the reaction mixture was stirred at ambient temperature for 1.5-2 h. Then the reaction mixture was poured into water (15 ml) and extracted into methylene chloride (3×20 ml). Organic extract was washed with water and brine and dried over magnesium sulfate. Solvent was then removed by rotary evaporation and the oil obtained was purified by column chromatography on silica (30 g, EtOAc/hexane 1:3) to give 190 mg of pure product as dark brown-purple solid. Yield 75%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07517992B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-e34ecffc335d410c99c7e77bd21657fc |
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| Source note | uspto-grants-2009_04 |
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