Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylamine | HCID 6341 | — |
| Reactant | Chloroacetyl chloride | HCID 6577 | — |
| Reactant | Malononitrile | HCID 8010 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178462792 | HCID 178462792 | 97.6% |
Reaction Steps
19.8 g of malononitrile were dissolved in 30 ml of DMF and cooled to 0° C. While cooling, 61 g of triethylamine and 32 g of chloroacetyl chloride were simultaneously added dropwise to this, and the mixture was then stirred at 10° C. for 10 minutes. Subsequently, while cooling, 49 g of 70% by weight aqueous ethylamine solution were added dropwise, and the mixture was stirred at room temperature for 8 hours. The precipitate was filtered off with suction, washed and dried at 50° C. 41.8 g (92%) of impure crude product were obtained and were recrystallized from 1:1 isopropanol/water with the addition of active carbon. This resulted in 10.9 g (24% of theory) of the compound of the formula ##STR23## of melting point 278° to 280° C. The IR, NMR, UV and mass spectra and the elemental analysis are consistent with the structural formula.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05003081 |
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| Source dataset | uspto-grants-1991_03 |
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| ORD ID | ord-063cb2d1013143d7b1127d42980e9336 |
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| Source note | uspto-grants-1991_03 |
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