Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | 1360953-55-4 | HCID 20369169 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | HCID 18408150 | HCID 18408150 | — |
Reaction Steps
A mixture of 248 (550 mg, 2.38 mmol), Pd(PPh3)4 (275 mg, 0.238 mmol), and Zn(CN)2 (279 mg, 2.38 mmol) in NMP (10 mL) was stirred under nitrogen atmosphere at 120° C. for 18 h. The reaction mixture was poured into water (50 mL), extracted with EtOAc (3×20 mL), and concentrated to dryness in vacuo. The crude was purified by SiO2 chromatography eluting with DCM:MeOH (12:1) to afford 217 mg (51.5%) of 6-chloro-1H-benzo[d]imidazole-5-carbonitrile (250) as yellow solid (217 mg, 51.5%): MS (ESI) m/z=178.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08637537B2 |
|---|
| Source dataset | uspto-grants-2014_01 |
|---|
| ORD ID | ord-233da9b2db8a4a308d330ce5e74e5465 |
|---|
| Source note | uspto-grants-2014_01 |
|---|