Triethylamine → HCID 58443686, compound

HRID 2381254Notes

Reaction equation

HRID 2381254 reaction equation
[CH3:1][O:2][NH:3][CH:4]([CH3:16])[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:24][CH:25]([F:35])[C:26]1[C:30]([C:31](Cl)=[O:32])=[CH:29][N:28]([CH3:34])[N:27]=1>ClCCl.O>[CH3:1][O:2][N:3]([CH:4]([CH3:16])[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:31]([C:30]1[C:26]([CH:25]([F:35])[F:24])=[N:27][N:28]([CH3:34])[CH:29]=1)=[O:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 58443691HCID 58443691, compound

Product 1

HCID 58443686HCID 58443686, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of O-Methyl-N-[1-methyl-3-(2,4,6-trichloro-phenyl)-propyl]-hydroxylamine (0.6 g, 2.1 mmol) prepared as described in example P23d, in dichloromethane (6 ml), was added triethylamine (0.73 ml, 5.2 mmol) followed by drop wise addition of a solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.415 g, 2.1 mmol) in dichloromethane at 0° C. After complete addition of acid chloride, the reaction mixture was stirred for 18 hours at ambient temperature. When the TLC confirmed 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 sat NaHCO3 then water and finally brine solution, dried over sodium sulfate and solvent was evaporated off under reduced pressure. The resulting crude mass was purified by column chromatography using 60-120μ mesh silica gel and product collected at 30% ethyl acetate in hexane as eluent to give 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-3-(2,4,6-trichloro-phenyl)-propyl]amide (0.53 g, 57%) as a gum like mass.

Workup

  1. customcompletion of the reaction
  2. extractionextracted with dichloromethane (3×60 ml)
  3. washThe combined dichloromethane layer was washed with 2N HCl
  4. dry with materialwater and finally brine solution, dried over sodium sulfate and solvent
  5. customwas evaporated off under reduced pressure
  6. customThe resulting crude mass was purified by column chromatography
  7. customcollected at 30% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-61c3519996cb48f6839514b204791e59
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

Loading…