Dicyclohexylcarbodiimide → Methyl 1-(4-bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12]2)=[O:10])=[C:4]([CH3:17])[CH:3]=1.[CH:18]1(N=C=NC2CCCCC2)CCCCC1>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([O:16][CH3:18])=[O:15])[CH2:12][CH2:13]2)=[O:10])=[C:4]([CH3:17])[CH:3]=1Participants
4
Procedure
A 4.00 gram (0.01 mole) portion of 1-(4-bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylic acid prepared in Example VIII (Compound 111) was reacted in sequence with 80 milliliters of methanol (excess as solvent) and 2.77 grams (0.01 mole) of 1,3-dicyclohexylcarbodiimide, employing a 16-hour reaction period, in a manner similar to that described in Example XL to give 1.54 grams (0.005 mole) of methyl 1-(4-bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylate as a white powder having a melting point of 106° C.-108° C. Elemental analysis of the product indicated the following: