Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | HCID 15481247 | HCID 15481247 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Product | HCID 18687789 | HCID 18687789 | 82% |
Reaction Steps
A suspension of 11-(3,5-diiodo-4-methoxy-phenyl)-benzo[b]naphtho[2,3-d]thiophene (4.55 g, 7.68 mmol) and copper (I) cyanide 3.13 g, 38.4 mmol) in 1-methyl-2-pyrrolidinone (18 mL) was heated in an 150° C. oil bath under a dry nitrogen atmosphere. After 1 h the solution was added to water (200 mL) and acidified with 10% aqueous HCl. The solid was filtered and flash chromatographed (silica gel: eluent: methylene chloride) to provide the title compound as a yellow solid (2.47 g, 82%): mp 214-215° C.: MS (EI): [M+], 390 (100%, MI); Anal. Calc. for C25H14N2OS: C, 76.90, H, 3.61, N, 7.17. Found: C, 76.48, H, 3.46, N, 7.17.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06110962 |
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| Source dataset | uspto-grants-2000_08 |
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| ORD ID | ord-073d0525c8ee4fdc8313f6bc7cb06e32 |
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| Source note | uspto-grants-2000_08 |
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