Water → HCID 57900754, compound

HRID 908099Notes

Reaction equation

HRID 908099 reaction equation
[H-].[Na+].[CH3:3]I.[CH:5]12[CH2:11][CH:8]([CH2:9][CH2:10]1)[CH2:7][CH:6]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]([C:21]1[C:22]([CH:27]([F:29])[F:28])=[N:23][N:24]([CH3:26])[CH:25]=1)=[S:20].O>CN(C)C=O.C1CCCCC1.C(OCC)(=O)C>[CH:5]12[CH2:11][CH:8]([CH2:9][CH2:10]1)[CH2:7][CH:6]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]([C:21]1[C:22]([CH:27]([F:29])[F:28])=[N:23][N:24]([CH3:26])[CH:25]=1)[S:20][CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19754686HCID 19754686, compound

Product 1

HCID 57900754HCID 57900754, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

At 0° C., 0.1 g (3.6 mmol) of sodium hydride (80% pure) and 1.2 g (8.3 mmol) of methyl iodide in 5 ml of dimethylformamide are added to a solution consisting of 1.0 g (2.8 mmol) of N-(2-bicyclo[2.2.1]hept-2-ylphenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-thiocarboxamide in 10 ml of dimethylformamide. The reaction mixture is slowly warmed to room temperature and stirred at this temperature for 1 hour. For work-up, the reaction mixture is poured into water and extracted three times with in each case 50 ml of ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. Column chromatography (cyclohexane/ethyl acetate 4:1) gives 0.7 g (1.9 mmol, 67% of theory) of methyl N-(2-bicyclo[2.2.1]hept-2-ylphenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbimidothioate [logP (pH 2.3)=4.75].

Workup

  1. extractionextracted three times with in each case 50 ml of ethyl acetate
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7885944f8084d8f9c4f70fd3d837a2c
Source dataset
uspto-grants-2011_09
Patent number
US08017558B2

Reaction notes

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