Formaldehyde → HCID 11999691, compound

HRID 1641745Notes

Reaction equation

HRID 1641745 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=2[F:17])=[CH:6][N:5]=[C:4]([C:27]([NH2:29])=[O:28])[CH:3]=1.C=O.[OH-].[Na+].[C:34](=O)([O-])[O-:35].[Na+].[Na+]>COCCOC>[OH:35][CH2:34][NH:29][C:27]([C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([CH:8]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:19])=[O:20])[C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=2[F:17])=[CH:6][N:5]=1)=[O:28]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 57736412HCID 57736412, compound

Product 1

HCID 11999691HCID 11999691, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-methyl-5-[(phenylsulfonyl)(2,3,6-trifluorophenyl)methyl]pyridine-2-carboxamide (215 mg, 0.51 mmol) in ethylene glycol dimethyl ether (6 ml), an aqueous solution of formaldehyde (37%, 0.2 ml) and 5% aqueous sodium hydroxide (0.8 ml) were added at 0° C., and the mixture was stirred for 1 hour at room temperature. Sodium carbonate (40 mg) was added to the reaction mixture, and the mixture was stirred for 20 minutes at room temperature. The mixture was concentrated under reduced pressure, and then the residue was dissolved in chloroform, dried over magnesium sulfate, and filtered. Subsequently, the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=1:2 was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether, and then was collected by filtration, to obtain the title compound (90 mg, 0.20 mmol, 39%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 20 minutes at room temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationSubsequently, the filtrate was concentrated under reduced pressure
  7. customThe fraction obtained from an elution with hexane
  8. concentrationethyl acetate=1:2 was concentrated under reduced pressure
  9. washthe resulting residue was washed with diethyl ether
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-29cf1dd8be87422ea1e6e1738002cf24
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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