Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Isothiocyanatotrimethylsilane | HCID 75297 | — |
| Reactant | (Z)-Ethyl 3-((2-amino-2-oxoethyl)amino)-3-(2-(2-hydroxyethoxy)phenyl)acrylate | HCID 86684693 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86684694 | HCID 86684694 | 31.7% |
Reaction Steps
To a solution of (Z)-ethyl 3-((2-amino-2-oxoethyl)amino)-3-(2-(2-hydroxyethoxy)phenyl)acrylate (1.0 g, 3.25 mmol) in tetrahydrofuran (15 mL) was added trimethylsilyl isothiocyanate (1.7 g, 12.9 mmol), and the mixture was stirred at 80° C. for 18 hours. The reaction mixture was cooled to room temperature, poured into a flask containing water and extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried and concentrated under reduced pressure to give a yellow solid, which was purified by flash chromatography (2-5% MeOH:CH2Cl2) to give the title compound (330 mg, 31.7%) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09399626B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-f0c16ce8fbfd49a2bd6c2be6faefe5ab |
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| Source note | uspto-grants-2016_07 |
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