Triethylamine → HCID 58443700, compound

HRID 2381255Notes

Reaction equation

HRID 2381255 reaction equation
[CH3:1][O:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=1[Cl:15].C(N(CC)CC)C.[F:23][CH:24]([F:34])[C:25]1[C:29]([C:30](Cl)=[O:31])=[CH:28][N:27]([CH3:33])[N:26]=1>ClCCl.O>[CH3:1][O:2][N:3]([CH2:4][CH2:5][CH2:6][C:7]1[C:8]([Cl:15])=[CH:9][C:10]([Cl:14])=[CH:11][C:12]=1[Cl:13])[C:30]([C:29]1[C:25]([CH:24]([F:34])[F:23])=[N:26][N:27]([CH3:33])[CH:28]=1)=[O:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 58443674HCID 58443674, compound

Product 1

HCID 58443700HCID 58443700, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of O-methyl-N-[3-(2,4,6-trichloro-phenyl)-propyl]-hydroxylamine (0.35 g, 1.3 mmol) prepared as described in example P24c in dichloromethane (5 ml), triethylamine (0.55 ml, 3.9 mmol) and a solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride acid in dichloromethane (2 ml) was added slowly at a temperature of 0° C. After complete addition of the acid chloride the mixture was stirred at ambient temperature for the next 3 hours. When the TLC confirmed the completion of the reaction, the reaction mass was diluted with water and extracted with dichloromethane (3×60 ml). The combined dichloromethane layer was washed with 2N HCl followed by saturated NaHCO3 solution, water and finally brine. The organic layer was then dried over anhydrous sodium sulphate and concentrated under reduced pressure. The resulting crude mass was purified over column chromatography (silica gel 60-120 mesh, 26% ethylacetate in hexane) to afford 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[3-(2,4,6-trichloro-phenyl)-propyl]-amide (0.5 g, 91%) as white crystalline solid. m.p-95-96° C.

Workup

  1. customthe completion of the reaction
  2. extractionextracted with dichloromethane (3×60 ml)
  3. washThe combined dichloromethane layer was washed with 2N HCl
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude mass was purified over column chromatography (silica gel 60-120 mesh, 26% ethylacetate in hexane)

Sources & evidence

ORD record
ord-a9a33cd8a02e42cf97d93bef479a76c4
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

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