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

HRID 1358600
Notes
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Reaction equation

HRID 1358600 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-3caf9c91215f4783b9dfc371fef00d98
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06596773B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes