Benzyl Bromide → HCID 14576597, compound

HRID 2292096Notes

Reaction equation

HRID 2292096 reaction equation
[F:1][C:2]1[C:3]([OH:22])=[C:4]([NH:9][CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O>[CH2:29]([O:22][C:3]1[C:2]([F:1])=[C:7]([F:8])[CH:6]=[CH:5][C:4]=1[NH:9][CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5338334HCID 5338334, compound

Product 1

HCID 14576597HCID 14576597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of diethyl N-(3,4-difluoro-2-hydroxyphenyl)aminomethylenemalonate (80 mg) and anhydrous potassium carbonate (70 mg) in dry dimethylformamide (1.5 ml) was added benzyl bromide (30 μl). The mixture was stirred at room temperature for 2 hours. After removal of the solvent under reduced pressure, the residue was dissolved in dichloromethane and the precipitate was filtered off. The filtrate was washed with water, dried over anhydrous sodium sulfate and evaporated. The crystalline residue was washed with n-hexane and recrystallized from methanol to give diethyl N-(2-benzyloxy-3,4-difluorophenyl)aminomethylenemalonate (90 mg), mp 87° C.; MS m/z 405 (M+).

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. filtrationthe precipitate was filtered off
  4. washThe filtrate was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. washThe crystalline residue was washed with n-hexane
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c975208fa282490ea6de9c5e937f623c
Source dataset
uspto-grants-1989_01
Patent number
US04801584

Reaction notes

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