Dimethylformamide → HCID 69522213, compound

HRID 856621Notes

Reaction equation

HRID 856621 reaction equation
[SH:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].Cl.Cl[CH2:15][C:16]1[N:20]([CH2:21][CH2:22][CH3:23])[CH:19]=[N:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:21]([N:20]1[CH:19]=[N:18][N:17]=[C:16]1[CH2:15][S:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12])[CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3048824HCID 3048824, compoundHCID 229387553-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochloride

Product 1

HCID 69522213HCID 69522213, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-mercapto-3-trifluoromethylaniline (1.0 g), 3-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochloride (1.1 g) and potassium carbonate (1.4 g) were added to N,N-dimethylformamide (35 ml), and the mixture was stirred overnight at room temperature. The mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then, the solvent was evaporated. The residue was purified by silica gel column chromatography (elution solvent: triethylamine/methanol/ethyl acetate) to give 4-[(4-propyl-4H-1,2,4-triazol-3-yl)methylthio]-3-trifluoromethylaniline (1.4 g) as pale brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (elution solvent: triethylamine/methanol/ethyl acetate)

Sources & evidence

ORD record
ord-fcc731197d274e719eb0d27844ad463a
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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