Water → HCID 70654337, compound

HRID 539447Notes

Reaction equation

HRID 539447 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH:12]([C:15]1[CH:16]=[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=[C:19]([CH:22]([CH3:24])[CH3:23])[C:20]=1[NH2:21])([CH3:14])[CH3:13].N1C=CC=CC=1.O>ClCCl>[CH:22]([C:19]1[CH:18]=[C:17]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:16]=[C:15]([CH:12]([CH3:14])[CH3:13])[C:20]=1[NH:21][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74374m-Anisoyl chlorideHCID 3025997Biphenyl, 3,5-diisopropyl-4-amino-

Product 1

HCID 70654337HCID 70654337, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-methoxybenzoyl chloride (7.54 mL, 55.3 mmol) in DCM (dichloromethane) (50 mL) was added slowly to a 0° C., stirred solution of 3,5-diisopropyl-[1,1′-biphenyl]-4-amine (10 g, 39.5 mmol) and pyridine (5.43 mL, 67.1 mmol) in DCM (100 mL). The mixture was then warmed up and stirred overnight at room temperature. After the reaction was complete, water was added into the reaction mixture. The aqueous mixture was extracted with DCM, and the DCM layer was separated, washed with water (2×), aq. Na2CO3, water (2×) and brine, and dried over anhydrous Na2SO4. Filtration and evaporation gave an off-white solid which was recrystallized from hexane/DCM (2/8) (v/v) to afford a snow white solid (9.93 g, 65%).

Workup

  1. temperatureThe mixture was then warmed up
  2. extractionThe aqueous mixture was extracted with DCM
  3. customthe DCM layer was separated
  4. washwashed with water (2×), aq. Na2CO3, water (2×) and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationFiltration and evaporation
  7. customgave an off-white solid which
  8. customwas recrystallized from hexane/DCM (2/8) (v/v)

Sources & evidence

ORD record
ord-a5639bbd9c034e3fa8d3a9905793fd12
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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