Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 2,4-Imidazolidinedione, 3-(hydroxymethyl)-1-(2-propynyl)- | HCID 11789597 | — |
| Reactant | HCID 86634960 | HCID 86634960 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 86634959 | HCID 86634959 | 54.5% |
Reaction Steps
Under nitrogen atmosphere, to a mixture of 0.12 g of 3-hydroxymethyl-1-(2-propynyl)imidazolidine-2,4-dione, 0.17 g of (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-(2-propynyloxyimino)-1-propenyl]cyclopropanecarboxylic acid, catalytic amount of 4-dimethylaminopyridine and 3 ml of anhydrous chloroform was added 0.16 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and the mixture was stirred at room temperature overnight. Thereafter, saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, then, filtrated, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.15 g of 2,5-dioxo-3-(2-propynyl)imidazolidin-1-ylmethyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-(2-propynyloxyimino)-1-propenyl]cyclopropanecarboxylate (hereinafter, referred to as the present compound (6)) represented by the formula (6):
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08039499B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-e8c3286157ed4665b14ec62e0e206ba2 |
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| Source note | uspto-grants-2011_10 |
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