Sodium Bicarbonate → HCID 23502800, compound

HRID 1835366Notes

Reaction equation

HRID 1835366 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](Cl)=[N:11][CH:10]=1.[CH3:34][S:35]([O-:37])=[O:36].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([S:35]([CH3:34])(=[O:37])=[O:36])=[N:11][CH:10]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2733271Sodium methanesulfinateHCID 10277890N-(3,5-bis-trifluoromethyl-benzyl)-6-chloro-N-methyl-4-o-tolyl-nicotinamide

Product 1

HCID 23502800HCID 23502800, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 369 mg (0.758 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-chloro-N-methyl-4-o-tolyl-nicotinamide (Example 2) and 176 mg (1.67 mmol) sodium methanesulfinate in 4 ml N,N-dimethylformamide was heated at reflux over night. After cooling to room temperature the mixture was diluted with dichloromethane and treated with saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with three portions of dichloromethane. The combined organic layers were dried with sodium sulfate, concentrated and and dried in high vacuo. Flash column chromatography gave 118 mg (29%) of the title compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux over night
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with three portions of dichloromethane
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. concentrationconcentrated
  7. customdried in high vacuo

Sources & evidence

ORD record
ord-31eecc30d6be4ecbaf93d64cdbe8f5d9
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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