Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 4-isothiocyanatobutanoate | HCID 123372 | — |
| Reactant | HCID 59463473 | HCID 59463473 | — |
| Catalyst | HCID 178418790 | HCID 178418790 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 11719232 | HCID 11719232 | — |
Reaction Steps
As depicted in Scheme 27 below, ethyl 2-(4-nitrophenyl)-4H-pyrrolo[2,3-d]thiazole-5-carboxylate (0.1 mmol) is placed in a heavy-walled glass tube equipped with a threaded Teflon plug, and ethyl 4-isothiocyanatobutyrate (1.03 mmol, 10 molequivalents) and triethylamine (2 mmol, 20 molequivalents) are added thereto. The glass tube is sealed and the reaction mixture is heated at 130° C. while stirring overnight (18 hours). Additional isothiocyanate (10 drops, 10 molequivalents) is added thereafter and heating is continued while stirring at 130° C. for 6 additional hours. The mixture is then dissolved in chloroform and the purified final product is isolated by column chromatography on silica, using a 9:1 hexane:ethyl acetate mixture as eluent.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07795255B2 |
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| Source dataset | uspto-grants-2010_09 |
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| ORD ID | ord-d8d5e4437fac4778b09023ec7ef29b39 |
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| Source note | uspto-grants-2010_09 |
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