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Dicyclohexylcarbodiimide → N-(2-benzoyl-4-chloro-phenyl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramide

HRID 2186775
Notes
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Reaction equation

HRID 2186775 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[F:17][C:18]([F:36])([F:35])[C:19]1[CH:20]=[C:21]([C:29]([CH3:34])([CH3:33])[C:30](O)=[O:31])[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCCl>[C:4]([C:3]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:2]=1[NH:1][C:30](=[O:31])[C:29]([C:21]1[CH:20]=[C:19]([C:18]([F:17])([F:35])[F:36])[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=1)([CH3:34])[CH3:33])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 128702-Amino-5-chlorobenzophenoneHCID 98359482-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid

Product 1

HCID 18185376N-(2-benzoyl-4-chloro-phenyl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramideYield 58%

Reagents, catalysts & solvents 1

HCID 11
1,2-Dichloroethane
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 233 mg (1 mmol) of 2-amino-5-chlorobenzophenone in 2 ml of 1,2-dichloroethane were added 360 mg (1.2 mmol) of 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionic acid and the reaction mixture was shaken at 80° C. for 1 h. Dicyclohexyl carbodiimide (194 mg, 1.2 mmol) was added and shaking was continued overnight at the same temperature. The solvent was evaporated and the residue obtained was purified by column chromatography on silica gel to yield 298 mg (58%) of the title compound as yellow oil.

Workup

  1. stirringshaking
  2. waitwas continued overnight at the same temperature
  3. customThe solvent was evaporated
  4. customthe residue obtained
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-372c97c6356243f5ba16c589fc52bf7e
Source dataset
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06407111B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes