Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethoxalyl chloride | HCID 20884 | — |
| Reactant | p-Toluohydrazide | HCID 77174 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66653417 | HCID 66653417 | 81% |
Reaction Steps
4-Methylbenzohydrazide (6 g, 40 mmol) was dissolved in DCM (100 mL) and triethylamine (7.3 g, 80 mmol) was added. The solution was cooled with an ice-bath and ethyl chloro(oxo)acetate (5.5 g, 40 mmol) was added dropwise. After completed addition the reaction was stirred at 0° C. for 1 h and at rt for 2 h. The reaction mixture was washed with 0.2 M HCl, aqueous NaHCO3 solution (sat.) and brine. The organic solution was filtered through a phase separator and the solvent was removed by evaporation. There was obtained 8.1 g (81%) of 6A as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.36 (t, 3H), 2.38 (s, 3H), 4.35 (q, 2H) 7.21 (d, 2H), 7.73 (d, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546375B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-46cf61d4084a42e69eb9f016c030693b |
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| Source note | uspto-grants-2013_10 |
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