HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methylcyclopropane-1-carbonyl chloride → 2-[p-(1-Methylcyclopropylcarbonylamino)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methylcyclopropane-1-carbonyl chloride | HCID 12789939 | — |
| Reactant | 5-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one | HCID 20264844 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-[p-(1-Methylcyclopropylcarbonylamino)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one | HCID 23458518 | 53.3% |
Reaction Steps
6.0 g (29.8 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one, 4.2 g (35.4 millimoles) of 1-methylcyclopropanecarboxylic acid chloride and 150 ml of absolute tetrahydrofuran are refluxed for 7 hours. The product is filtered off at 10° C., washed with water and recrystallized twice from a dimethylformamide/water mixture. 4.5 g (53% of theory) of 2-[p-(1-methylcyclopropylcarbonylamino)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are obtained as pale beige crystals, of melting point 253°-255° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04271163 |
| Source dataset | uspto-grants-1981_06 |
| ORD ID | ord-eea64af68f45451eaa4acd67e94445a7 |
| Source note | uspto-grants-1981_06 |