Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | tert-Butyl bromoacetate | HCID 79177 | — |
| Reactant | HCID 18930549 | HCID 18930549 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 53770272 | HCID 53770272 | 92% |
Reaction Steps
To a solution of N-(2-iodophenyl)-2-(3-m-tolylureido)acetamide (1.02 g, 2.5 mmol) in DMSO (5 ml) are added at room temperature potassium iodide (83 mg, 0.2 mmol), tetra-n-butylammonium bromide (81 mg, 0.1 mmol), t-butylbromoacetate (0.55 ml, 3.75 mmol) and potassium carbonate (1.04 g, 7.5 mmol), and stirred at room temperature for 2.25 hours. To the reaction mixture are added water and ethyl acetate, and the pH is adjusted to 2 with 2N hydrochloric acid. The aqueous layer is extracted twice with ethyl acetate. The organic layer is washed with 0.1N hydrochloric acid, water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated. To the residue is added isopropylether, and the precipitated solid is filtered off to obtain the objective compound (1.20 g). Yield 92%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05739162 |
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| Source dataset | uspto-grants-1998_04 |
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| ORD ID | ord-7bda12a7c0fc4d3d93900e4523bc204e |
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| Source note | uspto-grants-1998_04 |
|---|