Sodium Hydroxide → 3-(Difluoromethyl)-N-methoxy-1-methyl-N-(1-methyl-2-(2,4,6-trichlorophenyl)ethyl)-1H-pyrazole-4-carboxamide

HRID 2170305Notes

Reaction equation

HRID 2170305 reaction equation
[CH3:1][O:2][NH:3][CH:4]([CH3:15])[CH2:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[Cl:14].[OH-].[Na+].[F:18][CH:19]([F:29])[C:20]1[C:24]([C:25](Cl)=[O:26])=[CH:23][N:22]([CH3:28])[N:21]=1>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][N:3]([CH:4]([CH3:15])[CH2:5][C:6]1[C:7]([Cl:14])=[CH:8][C:9]([Cl:13])=[CH:10][C:11]=1[Cl:12])[C:25]([C:24]1[C:20]([CH:19]([F:29])[F:18])=[N:21][N:22]([CH3:28])[CH:23]=1)=[O:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 58443683N-methoxy-1-(2,4,6-trichlorophenyl)propan-2-amine

Product 1

HCID 569334113-(Difluoromethyl)-N-methoxy-1-methyl-N-(1-methyl-2-(2,4,6-trichlorophenyl)ethyl)-1H-pyrazole-4-carboxamideYield 88.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
56 °C

Procedure

To a solution of O-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]-hydroxylamine (3.92 g, 0.014 mol) prepared as described in example P5a in xylene (30 g) was added an aqueous sodium hydroxide solution (30%, 2.3 g, 0.017 mol) in parallel to the addition of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (3.2 g, 0.046 mol) dissolved in xylene (10 g) at 56° C. during 2 hours. After complete addition of acid chloride the mixture was stirred 2 hours at 56° C. The solution was washed twice with water (10 and 5 g) and the volatiles were removed from the organic layer under reduced pressure. The resulting crude mass 7.4 g (sticky dark brown oil) was purified by crystallization from a mixture of xylene (7 g) and methylcyclohexene (14 g) to give 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]amide (5.3 g, 87.8%) as off white solid. m.p: 115-116° C.

Workup

  1. washThe solution was washed twice with water (10 and 5 g)
  2. customthe volatiles were removed from the organic layer under reduced pressure
  3. customThe resulting crude mass 7.4 g (sticky dark brown oil) was purified by crystallization from a mixture of xylene (7 g) and methylcyclohexene (14 g)

Sources & evidence

ORD record
ord-424f06300ed2427db7eb0b351575d901
Source dataset
uspto-grants-2015_06
Patent number
US09051272B2

Reaction notes

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