1,1'-Carbonyldiimidazole → HCID 18185383, compound

HRID 1358615Notes

Reaction equation

HRID 1358615 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][C:14](O)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38]2[C:43]([NH2:44])=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:33][CH:32]=1>O1CCCC1>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([NH:44][C:43]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[NH:37][C:34]2[CH:33]=[CH:32][CH:31]=[CH:36][CH:35]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 68297N-Phenyl-o-phenylenediamineHCID 1235873,5-Bis(trifluoromethyl)phenylacetic acid

Product 1

HCID 18185383HCID 18185383, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 545 mg (2.0 mmol) 3,5-bis(trifluoromethyl)phenylacetic acid in 2 ml tetrahydrofuran at 0° C. were added 325 mg (2.0 mmol) 1,1′-carbonyldiimidazole. After stirring for 2.5 h at room temperature, 305 mg (1.66 mmol) 2-aminodiphenylamine were added and stirring was continued for 8 h at 60° C. The solvent was removed in vacuo and the residue was purified by flash chromatography to give 480 mg (66%) of the title compound as white crystals.

Workup

  1. stirringstirring
  2. waitwas continued for 8 h at 60° C
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-383dc97d49944856824e87945f3557b4
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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