Sodium Bicarbonate → HCID 22054196, compound

HRID 1830385Notes

Reaction equation

HRID 1830385 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:40])[C:5]([CH3:39])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:35]C(=O)C)=[C:17]([CH:34]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([C:30]([F:33])([F:32])[F:31])(=[O:29])=[O:28])=[CH:23][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:40])[C:5]([CH3:39])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([OH:35])=[C:17]([CH:34]=2)[C:18]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([S:27]([C:30]([F:31])([F:32])[F:33])(=[O:28])=[O:29])=[CH:25][CH:26]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054336HCID 22054336, compound

Product 1

HCID 22054196HCID 22054196, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(trifluoromethylsulfonyl)aniline (0.060 g, 0.103 mmol) was dissolved in methanol (3 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (2 ml), the solution was stirred at room temperature for 2 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 (chloroform:methanol=10:1) and then recrystallized from ether to obtain the titled compound (0.021 g, 0.0389 mmol, 38%).

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 (chloroform:methanol=10:1)
  8. customrecrystallized from ether

Sources & evidence

ORD record
ord-c83b3254275f4ea08d364c94af122c47
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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