Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 3-aminobenzoate | HCID 11400 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | HCID 21201778 | HCID 21201778 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 21201727 | HCID 21201727 | 200.7% |
Reaction Steps
Ethyl 3-aminobenzoate (0.54 g) was dissolved in tetrahydrofuran (15 ml), the solution was cooled to internal temperature 5-8° C. Triphosgene (0.35 g) was added, the mixture was stirred for 5 minutes. Subsequently, triethylamine (1.20 g) was added to the mixture over 15 minutes interval, stirred at room temperature for 10 minutes, and a solution of 1-(2-thenoylmethyl)-2-oxo-3-amino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.26 g) in tetrahydrofuran (15 ml) was added, stirred for one hour. Water and chloroform were added to the reaction mixture, and extracted. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, crystals so precipitated were collected by filtration with ether, to thereby obtain 1.46 g of the title compound (Yield: 79.8%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06239131B1 |
|---|
| Source dataset | uspto-grants-2001_05 |
|---|
| ORD ID | ord-634cd86108f94361bc8be7f861a8ee12 |
|---|
| Source note | uspto-grants-2001_05 |
|---|