Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | 4-Bromo-2-fluorobenzonitrile | HCID 736029 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178513246 | HCID 178513246 | 144.8% |
Reaction Steps
To a solution of 4-Bromo-2-fluorobenzonitrile 11 (800 g, 4 mol, 1 eq), hydroxylamine hydrochloride (695 g, 10 mol, 2.5 eq) in MeOH (2 L, 2.5 vol) was added Et3N (485 g, 4.8 mol, 1.2 eq), then the mixture was stirred at 60° C. for 40 min and checked by HPLC (no nitrile remaining) Reaction was then quenched by H2O (30 L), and lots of off-white solid was separated out, and then filtered, the filter cake was washed with water (10 L×2) and 1350 g wet 4-bromo-2-fluoro-N-hydroxybenzimidamide 24 was obtained with 96% purity
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09303043B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-0cb8212eaed24edca1057f0830265bc1 |
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| Source note | uspto-grants-2016_04 |
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