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ChemicalBook CAS DataBase List 4-BROMOPHENYLUREA
1967-25-5

4-BROMOPHENYLUREA synthesis

12synthesis methods
p-Bromophenylurea is obtained by heating p-bromoaniline and sodium cyanate in glacial acetic acid.
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Yield: 73%

Reaction Conditions:

with [bis(acetoxy)iodo]benzene;ammonia in methanol at 0 - 20; for 2 h;Inert atmosphere;Hofmann Rearrangement;

Steps:

N-Substituted Ureas; General Procedure A
General procedure: (Diacetoxyiodo)benzene (1.0 mmol, 2.0 equiv) was added in one portion to a stirred solution of the amide (0.5 mmol, 1.0 equiv) in NH3/MeOH (7 M, 1.25 mL, 17.5 equiv) at 0 °C under argon. After 30 min at 0 °C, the reaction mixture was allowed to reach room temperature and was left to stir for 90 min. After completion (monitored by TLC and 1H NMR), the reaction mixture was concentrated under reduced pressure and the crude product was purified by flash chromatography on silica gel.

References:

Franck, Xavier;Glachet, Thomas;Ibert, Quentin;Lohier, Jean-Fran?ois;Reboul, Vincent;Saraiva Rosa, Nathalie [Synthesis,2020,vol. 52,# 14,p. 2099 - 2105]

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