Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,3-Cyclohexanedione | HCID 10434 | — |
| Reactant | 2-Chloro-4-fluorobenzaldehyde | HCID 145024 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | 1,3-Thiazole-2-carboximidamide hydrochloride | HCID 18679584 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68525469 | HCID 68525469 | 27% |
Reaction Steps
2-thiazolecarboxamidine hydrochloride (Schaefer P. C., Peters G. A., et al.) 2.164 mmol, 2-chloro-4-fluorobenzaldehyde 2.164 mmol, 1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml anhydrous ethanol under refluxing for 18 hr, and condensed, to which ethyl acetate and water and 1N HCl were added and the layers were separated. The water layer was adjusted with concentrated NaOH solution until pH value to be basic, then ethyl acetate was added again and extracted twice. The organic layers were combined, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain a yellow crystal of 0.21 g (yield 27%); 1H-NMR (400 MHz, CDCl3-d1) δ 7.86 (m, 1H, ArH); 7.73-7.52 (m, 1H, ArH); 7.24-7.21 (m, 1H, ArH); 7.15-7.12 (m, 1H, ArH); 6.94-6.92 (m, 1H, ArH); 6.11 (s, 1H, CH); 2.80-2.47 (m, 2H, CH2); 2.14-2.11 (m, 2H, CH2). HREI: 361.0450 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08188091B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-61e4e8b1f5b345af81ff6ecf57753b8c |
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| Source note | uspto-grants-2012_05 |
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