Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3,3-Dimethyl-1-butyne | HCID 13512 | — |
| Reactant | HCID 86693804 | HCID 86693804 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86693803 | HCID 86693803 | 23.6% |
Reaction Steps
Dimethylformamide (10 ml), 10 ml of triethylamine, 0.27 g of tert-butylacetylene, 0.11 g of palladium chloride-ditriphenylphosphine complex, and 0.03 g of copper iodide were added to 0.50 g of the N-ethyl-N-methyl-N′-(4-iodo-2-methylphenyl)formamidine (Compound 2-2) produced in Reference Example 2, and the mixture was stirred at 80° C. for 12 hours. After completion of the reaction, water was added to the reaction solution, and extraction was performed 3 times with ethyl acetate. The organic layer was collected, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), thereby obtaining 0.10 g of N-ethyl-N-methyl-N′-[2-methyl-4-(3,3-dimethyl-1-butynyl)phenyl]formamidine (Compound 66).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09169276B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-1039f1e186f34c7c8c6c9f37b1fe0a94 |
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| Source note | uspto-grants-2015_10 |
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