Synthesis of benzoyl azide

Preparation of benzoyl azide

A solution of 37 g. (0.57 mole) of sodium azide in 100 ml. of distilled water is cooled to 0° and added to a solution of 70 g. (0.50 mole) of benzoyl chloride in 125 ml. of acetone also at 0°. The mixture is held at 0° and shaken occasionally over a period of 30 minutes. The organic layer is separated and poured on crushed ice. The precipitated benzoyl azide is removed by filtration and recrystallized from a mixture of acetone and water to give 40 g. (47%) of product melting at 32°.

Reference: J. Am. Chem. Soc, 63, 3434 (1941).

IUPAC Name

benzoyl azide

InChI

InChI=1S/C7H5N3O/c8-10-9-7(11)6-4-2-1-3-5-6/h1-5H

InChI Key

PJHUABJTDFXYRQ-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(=O)N=[N+]=[N-]

Depositor-Supplied Synonyms

BENZOYL AZIDE, 582-61-6, Benzoic acid azide, Benzoyl azide solution, PJHUABJTDFXYRQ-UHFFFAOYSA-N, Benzoyl azide [Forbidden], benzoylazide, Benzazide, Benzazide solution, azido-phenyl-methanone, N-DIAZOBENZAMIDE, AC1L1ULC, Benzoic acid azide solution, SCHEMBL13449660, CTK3I9352, DTXSID00206944, ZINC15784780, AKOS009454274, HE356040

Removed Synonyms

CID61132

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