HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 475189Generated: October 30, 2026
N-methyl-2-pyrrolidone → 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-4-carbonitrile
https://huagongshe.com/reaction/475189
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | 4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole | HCID 71272186 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-4-carbonitrile | HCID 71272152 | 70% |
Reaction Steps
A mixture of 54 (1.30 g, 4.62 mmol), Zn(CN)2 (1.08 g, 9.24 mmol), Pd(PPh3)4 (0.53 g, 0.46 mmol) and NMP (15 mL) was stirred under nitrogen at 85° C. for 14 h. The mixture was filtered and the filtrate was purified by reverse phase chromatography eluting with 35% MeCN/H2O (containing 0.5% ammonia) to afford 0.75 g (70%) 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-4-carbonitrile (56) as brown solid: MS (ESI) m/z=228.3 [M+l]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08637537B2 |
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| Source dataset | uspto-grants-2014_01 |
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| ORD ID | ord-a65700297554431ea60b8238bbb984d6 |
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| Source note | uspto-grants-2014_01 |
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