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Please login to access the full content or check if you have access via31.28.1.33.5 Variation 5: Replacement of an Aromatic C—O Bond by a C—N Bond
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Scholz, U.; Schlummer, B., Science of Synthesis, (2007) 31, 1652.
The rearrangement of N-arylbenziminoaryl ethers to benzoyldiarylamines matches the scheme of replacement of a C—O bond with a C—N bond. This type of rearrangement is sometimes referred to as the Chapman rearrangement and is exemplified by the synthesis of 2-[(4-chlorophenyl)amino]benzoic acid (205) from the sodium salt of methyl salicylate and N-(4-chlorophenyl)benzenecarboximidoyl chloride (202) at room temperature. The phenolate first forms the imino ester 203 in 88% yield; the temperature is then increased to 270–275°C to induce the rearrangement to methyl 2-[benzoyl(4-chlorophenyl)amino]benzoate (204) in 85–91% yield. Subsequent quantitative hydrolysis of the amide and ester bonds using sodium hydroxide yields 205 (Scheme 222).[396]
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References
| [396] | Meeeeee, M. M.; Meeeee, M. M., M. Meee. Mee., (8888), 8888. |
| [397] | Meeee, M.; Meeeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
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