Triethylamine → HCID 58443666, compound

HRID 2381253Notes

Reaction equation

HRID 2381253 reaction equation
[CH2:1]([O:3][NH:4][CH:5]([CH3:16])[CH2:6][C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=1[Cl:15])[CH3:2].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>[CH2:1]([O:3][N:4]([CH:5]([CH3:16])[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])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 86657767HCID 86657767, compound

Product 1

HCID 58443666HCID 58443666, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of O-ethyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]-hydroxylamine (0.5 g, 1.63 mmoles) in dichloromethane (5 ml) was added triethylamine (0.566 ml, 4.07 mmloes) followed by drop wise addition of a solution 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.34 g, 1.79 mmol) in dichloromethane at a temperature of 0° C. After the complete addition of acid chloride the 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 were washed with 2N HCl, followed by saturated NaHCO3, then water and finally brine, dried over sodium sulfate and evaporated off solvent under reduced pressure. 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 ethoxy-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]-amide (0.390 g, 50%) as off white solid. m.p: 111-114° C.

Workup

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

Sources & evidence

ORD record
ord-9f99d6a157754c4cb3d1e017ac085b21
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

Loading…