Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66747606 | HCID 66747606 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66747459 | HCID 66747459 | 103.7% |
Reaction Steps
To a solution of ethyl 4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazole-5-carboxylate (430 mg, 1.20 mmol) in DMF (6.0 mL) was added mCPBA (322 mg, 1.44 mmol) and the mixture was stirred at room temperature overnight. To the reaction was added DCM (30 mL) and saturated sodium bicarbonate (25 mL). The layers were separated and the aqueous layer extracted with DCM (20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/DCM=50/50→100/0) to give 449 mg of the title compound as a white solid (100% yield). LC/MS (FA) ES+ 375. 1H NMR (300 MHz, CDCl3) δ: 8.23-8.20 (m, 2H), 7.84-7.81 (m, 2H), 7.33-7.23 (m, 4H), 4.51 (s, 2H), 4.38 (q, 2H, J=7.2 Hz), 1.39 (t, 3H, J=7.2 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796268B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-5e3429588ff94e9a9ed9ef78c5ac0d77 |
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| Source note | uspto-grants-2014_08 |
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