HuagongsheHuagongshe Chemistry Print Report · For research reference only
18-Crown-6 → 2-(3-Fluoro-4-nitrobenzamido)acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | Potassium 2-(3-iodyl-4-nitrobenzamido)acetate | HCID 86713125 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 2-(3-Fluoro-4-nitrobenzamido)acetic acid | HCID 15925739 | 71.8% |
Reaction Conditions
| Temperature | 105 °C |
|---|
Reaction Steps
A mixture of spray-dried KF (138 mg, 2.3 mmol), intermediate 9 (100 mg, 0.23 mmol), catalytic amount of 18-crown-6 in dry DMSO (4 mL) was stirred at 100-110° C. for 15 min. Work-up of the reaction mixture as described in example 1 gave the product as a colorless solid (40 mg, 69%), mp 136-138° C. 1H NMR (400 MHz, DMSO-d6): δ 8.76 (1H, br s), 8.25 (1H, t, J=7.8 Hz), 8.00 (1H, d, J=12.0 Hz), 7.90 (1H, d, J=8.4 Hz), 3.75 (2H, d, J=4.4 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08906344B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-81b4dab56447427b84a581d3ac64b754 |
| Source note | uspto-grants-2014_12 |