HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1961487Generated: October 31, 2026
Tert-Butyl nitrite → tert-Butyl 4-azido-3-iodobenzylcarbamate
https://huagongshe.com/reaction/1961487
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tert-Butyl nitrite | HCID 10906 | — |
| Reactant | Azidotrimethylsilane | HCID 78378 | — |
| Reactant | tert-Butyl 4-amino-3-iodobenzylcarbamate | HCID 10383091 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | tert-Butyl 4-azido-3-iodobenzylcarbamate | HCID 86661980 | 87.2% |
Reaction Steps
tert-Butyl 4-amino-3-iodobenzylcarbamate (1.0 g, 2.87 mmol) was dissolved in CH3CN (6.0 ml). The solution was cooled to 0° C., tert-butyl nitrite (444.3 mg, 4.30 mmol) and TMS azide (397.1 mg, 3.45 mmol) were added. The mixture was then stirred at r.t for 2.0 h. The solvents were removed under vacuum and the residue purified by flash chromatography (Pet. Ether/EtOAc 85:15) affording 936 mg (87%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415333B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-f1d7edcee4fb4b16bc6067874f8b8fdd |
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| Source note | uspto-grants-2013_04 |
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