HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → methyl 4-(1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 4-Methoxycarbonylphenyl isothiocyanate | HCID 138002 | — |
| Reactant | 1-N-(2-methoxyethyl)benzene-1,2-diamine | HCID 10261452 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | methyl 4-(1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)benzoate | HCID 67775781 | 68.9% |
Reaction Steps
N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide (EDC, 791 mg) is added to a solution of N1-(2-methoxyethyl)benzene-1,2-diamine (311 mg, 1.87 mmol) and methyl 4-isothiocyanatobenzoate (328 mg, 1.70 mmol) in tetrahydrofuran. The reaction may be heated to reflux for 2 hr and cooled to room temperature. The mixture may be diluted in an appropriate solvent such as ethyl acetate, filtered and concentrated. The residue may be purified by any appropriate method, including Biotage column chromatography to give methyl 4-(1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)benzoate (381 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09125901B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-60b3dfa705444ea9bde0239dfa76aafa |
| Source note | uspto-grants-2015_09 |