Operationally Simple Synthesis of <i>N</i>,<i>N</i>-Diethyl-3-methylbenzamide (DEET) Using COMU as a Coupling Reagent
Why this work is in the frame
A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.
Bibliographic record
Abstract
A novel procedure is described where students use COMU [(1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate], as a nonhazardous partner, in the one-pot coupling of a carboxylic acid and amine producing N, N -diethyl-3-methylbenzamide (DEET). Fundamental principles of carbonyl reactivity are understood, with potential for expansion to new methods of amide bond formation. The reaction can be monitored visually by virtue of the color change associated with the conversion, and all byproducts are conveniently water-soluble. This modern, microscale reaction is appropriate for a second-semester introductory undergraduate organic chemistry course: it can be performed during a 3 h laboratory period and is operationally straightforward. Curricular flexibility allows for this protocol to serve as a meaningful discussion of mechanistic organic chemistry and spectroscopy.
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Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.004 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it