Dicyclohexylcarbodiimide → HCID 21909973, compound

HRID 1245271Notes

Reaction equation

HRID 1245271 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:13][CH:12]=2)[C:8]([F:22])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:23][C:24]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])[CH:27]=[CH:26][C:25]=1O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:13][CH:12]=2)[C:8]([F:22])=[CH:7][C:3]=1[C:4]([O:6][C:25]1[CH:26]=[CH:27][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])=[CH:29][C:24]=1[F:23])=[O:5]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 219099662,5-Difluoro-4′-pentyl[1,1′-biphenyl]-4-carboxylic acidHCID 219099682',3-Difluoro[1,1'-biphenyl]-4-ol

Product 1

HCID 21909973HCID 21909973, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2,5-difluoro-4-(4-pentylphenyl)benzoic acid (28.40 mmol), 2-fluoro-4-(2-fluorophenyl)phenol (28.40 mmol), and dichloromethane (100 ml), 4-dimetylaminopyridine (34.10 mmol) is added dropwise. Then, a solution of 1,3-dicyclohexylcarbodiimide (34.10 mmol) in dichloromethane (100 ml) is added dropwise. After the addition is completed, the reaction mixture is stirred for 17 hrs at room temperature. Solid formed is filtered off, and a saturated aqueous solution of sodium chloride is added dropwise to the reaction mixture. The organic layer is washed with in the order of 3N-hydrochloric acid (300 ml), water, a saturated aqueous solution of sodium hydrogen carbonate (300 ml), and dried over anhydrous magnesium sulfate. The dichloromethane solution is concentrated under reduced pressure, purified by silica-gel chromatography, and further recrystallized to give the titled compound.

Workup

  1. additionis added dropwise
  2. additionAfter the addition
  3. customSolid formed
  4. filtrationis filtered off
  5. additiona saturated aqueous solution of sodium chloride is added dropwise to the reaction mixture
  6. washThe organic layer is washed with in the order of 3N-hydrochloric acid (300 ml), water
  7. dry with materiala saturated aqueous solution of sodium hydrogen carbonate (300 ml), and dried over anhydrous magnesium sulfate
  8. concentrationThe dichloromethane solution is concentrated under reduced pressure
  9. custompurified by silica-gel chromatography
  10. customfurther recrystallized

Sources & evidence

ORD record
ord-79cc224d0cb44b61a6f1f702d90b1974
Source dataset
uspto-grants-2006_10
Patent number
US07125589B1

Reaction notes

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