Development and Scale Up of a Route to Cyclohexylhydrazine Dimethanesulfonate
Bibliographic record
Abstract
A mild, high-yielding synthesis of cyclohexylhydrazine dimethanesulfonate has been developed that is suitable for further scale up. The process consists of three chemical steps: condensation of cyclohexanone with tert -butyl carbazate, reduction of the hydrazone carboxylate to a hydrazine carboxylate with borane−THF, and hydrolysis, decarboxylation, and derivatization with methanesulfonic acid. From studies using a reaction calorimeter, it was determined that the last stage of the process occurs in two discrete steps, requiring 2 equiv of methanesulfonic acid. The first equivalent of acid is consumed by N-protonation. Deprotection of the Boc group occurs with the second equivalent of acid, as evident by the gas evolution. The heat of reaction for the acid addition was determined to be 57.7 kJ/kg and represents an adiabatic temperature rise of 27.4 °C.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| 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 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 0.001 |
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 itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".