Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl isothiocyanate | HCID 10966 | — |
| Reactant | Methyl 4-aminobenzoate | HCID 12082 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 726326 | HCID 726326 | — |
Reaction Steps
To a solution of methyl 4-aminobenzoate (2-2) (30.2 mg, 0.20 mmol) in anhydrous acetonitrile (0.4 mL) is added ethyl isothiocyanate (2-1) (17.52 μL, 0.20 mmol) and the reaction mixture is heated at 80° C. overnight. After cooling to room temperature, the mixture is poured into water (50 mL) and extracted with ethyl acetate (EtOAc) (3×50 mL). The combined organic layers are washed with brine and dried using MgSO4. The drying agents are removed by filtration and the solvent is removed under vacuum. The resulting residue is then purified by flash column chromatography (silica gel, EtOAc/hexane, 0%-40%) to provide methyl 4-(3-ethylthioureido)benzoate (2-3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08362050B2 |
|---|
| Source dataset | uspto-grants-2013_01 |
|---|
| ORD ID | ord-87e1fef935c8443aaed448f76089c6aa |
|---|
| Source note | uspto-grants-2013_01 |
|---|