Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dimedone | HCID 31358 | — |
| 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 68528646 | HCID 68528646 | 28% |
Reaction Steps
2-thiazolecarboxamidine hydrochloride (Schaefer F. C., Peters G. A., et al.) 2.164 mmol, 2-chloro-4-fluorobenzaldehyde 2.164 mmol, 5,5-dimethyl-1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml of anhydrous ethanol under refluxing for 18 hr, condensed, to which ethyl acetate and water and 1N HCl were added, and separated. The water layer was adjusted with concentrated NaOH solution until pH value to be basic, then ethyl acetate was added and extracted twice. The organic layers were combined, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain a yellow crystal 0.23 g (yield 28%); 1H-NMR (400 MHz, CDCl3-d1) δ 7.95-7.85 (m, 1H, ArH); 7.64-7.47 (m, 1H, ArH); 7, 34-7.24 (m, 1H, ArH); 7.13-7.11 (m, 1H, ArH); 6.11 (s, 1H, CH); 2.70-2.52 (m, 2H, CH2); 2.43-2.26 (m, 2H, CH2); 1.15 (s, 6H, CH3). HREI: 389.0765 (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-36046b5b25c04ceabfeb4fd924006c24 |
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| Source note | uspto-grants-2012_05 |
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