Water → 5-(4-chloro-2-hydroxymethylphenylthio)-N-methyl-2-nitroaniline

HRID 1081881Notes

Reaction equation

HRID 1081881 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([CH2:9][OH:10])[CH:3]=1.F[C:12]1[CH:13]=[CH:14][C:15]([N+:20]([O-:22])=[O:21])=[C:16]([CH:19]=1)[NH:17][CH3:18].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:12]2[CH:13]=[CH:14][C:15]([N+:20]([O-:22])=[O:21])=[C:16]([CH:19]=2)[NH:17][CH3:18])=[C:4]([CH2:9][OH:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 133126194-Chloro-2-(hydroxymethyl)thiophenolHCID 229057745-fluoro-N-methyl-2-nitroaniline

Product 1

HCID 233631425-(4-chloro-2-hydroxymethylphenylthio)-N-methyl-2-nitroanilineYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of 4-chloro-2-(hydroxymethyl)thiophenol (1.0 g) from Example 16, 5-fluoro-N-methyl-2-nitroaniline (1.0 g) and K2CO3 (0.81 g) in DMF (20 ml) was heated at 90° C. for 15 minutes. After leaving the solution to stand at room temperature, water was added to the solution prior to extraction in ethyl acetate. The organic layer was washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was purified by chromatography on a silica gel column (methylene chloride) to give the title compound (1.62 g; 85%).

Workup

  1. customAfter leaving the solution
  2. customto stand at room temperature
  3. extractionto extraction in ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removal of the solvent under reduced pressure
  7. customthe residue was purified by chromatography on a silica gel column (methylene chloride)

Sources & evidence

ORD record
ord-a3415ebc969543aeaaf8fe816c1600b1
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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