Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 19386946 | HCID 19386946 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Propan-2-one--dichloromethane (1/1) | HCID 21584124 | — |
| Product | Sarakalim | HCID 10047015 | 44.9% |
Reaction Steps
A solution of 6-trifluoromethyl-2,2-dimethyl-3-(hydroxyamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.48 g, 1.31 mmol) in dichloromethane (13 ml) was cooled to 0° C. and treated with triethylamine (0.18 ml, 1.31 mmol) and acetyl chloride (0.1 ml, 1.31 mmol), and stirred at 0° C. for 45 minutes. Water was added, and the organic layer separated, washed with water and dried, and evaporated to give a crude product. Chromatography on silica gel eluting with dichloromethane/methanol (95/5) gave an oil which was crystallized from ether to give 0.24 g of 6-trifluoromethyl-2,2-dimethyl-3-(N-hydroxyacetamido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 188° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05250547 |
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| Source dataset | uspto-grants-1993_10 |
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| ORD ID | ord-13d241ec1da24160b239a06e373d3ced |
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| Source note | uspto-grants-1993_10 |
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