Dimethylformamide → 4-Hydroxy-3-methoxy-N,N-di(propan-2-yl)benzamide

HRID 2209737Notes

Reaction equation

HRID 2209737 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].S(Cl)(Cl)=O.CN(C)C=O.[CH:22]([NH:25][CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23]>ClCCl.C(OCC)(=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:25]([CH:26]([CH3:28])[CH3:27])[CH:22]([CH3:24])[CH3:23])=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 8468Vanillic AcidHCID 24386Thionyl Chloride

Product 1

HCID 217472594-Hydroxy-3-methoxy-N,N-di(propan-2-yl)benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 4-hydroxy-3-methoxy-benzoic acid (5 g, 29.7 mmol) in 35 mL of dichloromethane is treated with thionyl chloride (20 mL, 377 mmol) and N,N-dimethylformamide (1.0 mL, 12.9 mmol). This solution is refluxed for 45 minutes and concentrated in vacuo. The resulting material is dissolved in 125 mL of dichloromethane and treated with diisopropylamine (20 mL, 143 mmol). After stirring at room temperature for 5 minutes, the reaction is diluted with ethyl acetate and filtered. The filtrate is washed with 1N hydrochloride solution, and brine, dried over magnesium sulfate, and concentrated in vacuo to afford 4-hydroxy-3-methoxy-N,N-bis(1-methylethyl)benzamide as a colorless solid.

Workup

  1. temperatureThis solution is refluxed for 45 minutes
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting material is dissolved in 125 mL of dichloromethane
  4. filtrationfiltered
  5. washThe filtrate is washed with 1N hydrochloride solution, and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bece022673c647b69f66c0fdbccd122f
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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