Water → HCID 47467978, compound

HRID 453117Notes

Reaction equation

HRID 453117 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18]([Br:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C(#N)C>[CH2:18]([Br:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:18]([O:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 137262814-Chloro-2-hydroxybenzamide

Product 2

HCID 7498Benzyl BromideHCID 47467978HCID 47467978, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chloro-2-hydroxybenzamide (0.608 g, 3.54 mmol) in acetonitrile (50 ml) was added dried K2CO3 (1.71 g, 12.40 mmol) followed by benzyl bromide (0.63 ml, 5.32 mmol) and the resulting reaction mixture was refluxed at 80° C. for 16 h. After the completion of the reaction (TLC monitoring), water was added followed by extraction with EtOAc (3×100 ml). The combined organics was dried over anhydrous Na2SO4, filtered and concentrated. The residue was washed repeatedly with hexane to get rid of the excess of benzyl bromide resulting the desired product (0.75 g, 81%).

Workup

  1. customthe resulting reaction mixture
  2. additionwas added
  3. extractionfollowed by extraction with EtOAc (3×100 ml)
  4. dry with materialThe combined organics was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe residue was washed repeatedly with hexane

Sources & evidence

ORD record
ord-7f482b0b6c1e495baffb4737c430c5a2
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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