Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diiodomethane | HCID 6346 | — |
| Reactant | Isoamyl Nitrite | HCID 8053 | — |
| Reactant | HCID 59250010 | HCID 59250010 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 59250036 | HCID 59250036 | 37.2% |
Reaction Steps
To a suspension of ethyl 5-amino-4-cyano-3-(2,4-dichlorophenyl)thiophene-2-carboxylate (2.92 g, 0.00856 mol) in acetonitrile (10 mL) was added diiodomethane (2.41 mL, 0.0300 mol) under an atmosphere of argon and was heated at 38° C. Isoamyl nitrite (2.61 g, 0.0214 mol) was added dropwise and the reaction mixture was cooled to room temperature and stirred for one hour. The reaction was concentrated in vacuo and column chromatography was performed to yield the title compound (1.44 g, 37%) as an orange solid. 1H NMR (400 MHz, d1-chloroform) δ: 7.53 (d, 1H, J=2.00 Hz), 7.38-7.34 (m, 1H), 7.21 (d,1H, J=8.28 Hz), 4.25-4.15 (m, 2H), 1.21-1.16 (m, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08440664B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-a50083587a9d474795016d79a442b367 |
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| Source note | uspto-grants-2013_05 |
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