Water → HCID 85806873, compound

HRID 1353653Notes

Reaction equation

HRID 1353653 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O>CN(C)C=O>[C:10]1([C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:3][C:4]=2[C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:18])=[O:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22480166HCID 22480166, compound

Product 1

HCID 85806873HCID 85806873, compoundYield 144.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[4-hydroxy-2-(phenylcarbonyl)phenyl]benzamide (4.0 g, 12.6 mmol) in dimethyl formamide (DMF) (15 mL) was added potassium carbonate (K2CO3) (large excess) then benzyl bromide (660 μL, 5.5 mmol). The reaction was stirred overnight. It was added to water (100 mL) then extracted with ethyl acetate (3×40 mL). The combined organic layers were dried (Na2SO4) then concentrated under vacuo to give a solid which was recrystallized with ethyl acetate/hexane to give the title compound (3.24 g, 63% yield, analytical).

Workup

  1. extractionthen extracted with ethyl acetate (3×40 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationthen concentrated under vacuo
  4. customto give a solid which
  5. customwas recrystallized with ethyl acetate/hexane

Sources & evidence

ORD record
ord-7ccc3480e8e0437ea221d20a029835d6
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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