HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 506170Generated: October 26, 2026
3-Oxobutyronitrile → 5-(Dimethylamino)-2-(dimethylaminomethylidene)-3-oxopent-4-enenitrile
https://huagongshe.com/reaction/506170
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Oxobutyronitrile | HCID 75579 | — |
| Reactant | Dimethylformamide dimethyl acetal | HCID 78373 | — |
| Reactant | tert-Butoxy bis(dimethylamino)methane | HCID 79885 | — |
| Product | 5-(Dimethylamino)-2-(dimethylaminomethylidene)-3-oxopent-4-enenitrile | HCID 72297055 | 67.5% |
Reaction Steps
A mixture of acetoacetonitrile (41 g, 493 mmol), t-butoxybis(dimethyl amino)methane (86 g, 493 mmol) and DMF-DMA (263 mL, 1.97 mol) was heated at 100° C. overnight and evaporated to remove the volatiles. The residue was triturated with hexanes/ether (1:1) and the solids were collected by filtration and washed with hexanes/ether (1:1) and a minimum amount of EtOAc to give 64.3 g (67%) of 5-(dimethylamino)-2-[(dimethylamino)methylene]-3-oxopent-4-enenitrile as a light yellow solid, which was used for the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07781591B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-c6005b4fad4544b394938890aa4465f5 |
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| Source note | uspto-grants-2010_08 |
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