Sodium Bicarbonate → HCID 22054228, compound

HRID 1830335Notes

Reaction equation

HRID 1830335 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:41])[C:5]([CH3:40])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:36]C(=O)C)=[C:17]([CH:35]=2)[C:18]([NH:20][C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].C(=O)([O-])O.[Na+]>CO.O>[CH3:1][O:2][C:3]1[C:4](=[O:41])[C:5]([CH3:40])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([OH:36])=[C:17]([CH:35]=2)[C:18]([NH:20][C:21]2[CH:22]=[C:23]([C:31]([F:33])([F:34])[F:32])[CH:24]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:26]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054304HCID 22054304, compound

Product 1

HCID 22054228HCID 22054228, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-3,5-bistrifluoromethylaniline (0.130 g, 0.222 mmol) was dissolved in methanol (6 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (3 ml), the solution was stirred at room temperature for 3 hours. After the completion of reaction, the reaction solution was diluted with water and then extracted with ethyl acetate. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=1:2) and then recrystallized from ether to obtain the titled compound (0.050 g, 0.0921 mmol, 41%).

Workup

  1. additionafter adding
  2. customAfter the completion of reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was removed by distillation
  7. customThe obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=1:2)
  8. customrecrystallized from ether

Sources & evidence

ORD record
ord-b95b4a9ebbb54bd59b18c564476ee64a
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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