Dicyclohexylcarbodiimide → Methyl 1-(4-bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylate

HRID 893209Notes

Reaction equation

HRID 893209 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]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 190969071-(4-Bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylic acid2×

Product 1

HCID 19096841Methyl 1-(4-bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4.00 gram (0.01 mole) portion of 1-(4-bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylic acid prepared in Example VIII (Compound 111) was recited 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.

Workup

  1. waitemploying a 16-hour
  2. customreaction period

Sources & evidence

ORD record
ord-f31016362ac14ae09ecb154b602b8cee
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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