Water → 1,1-Dimethylethyl [3-[[3-cyano-6-(trifluoromethyl)-2-pyridinyl]oxy]pentyl]methylcarbamate

HRID 1243608Notes

Reaction equation

HRID 1243608 reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH:14][CH:15]([CH2:27][CH3:28])[CH2:16][CH2:17][N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].[H-].[Na+].O>CN(C)C=O>[C:4]([C:3]1[C:2]([O:14][CH:15]([CH2:27][CH3:28])[CH2:16][CH2:17][N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[N:9][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:7][CH:6]=1)#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrileHCID 857904251,1-Dimethylethyl (3-hydroxypentyl)methylcarbamate

Product 1

HCID 696559231,1-Dimethylethyl [3-[[3-cyano-6-(trifluoromethyl)-2-pyridinyl]oxy]pentyl]methylcarbamateYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-6-(trifluoromethyl)nicotinonitrile (207 mg) and 1,1-dimethylethyl (3-hydroxypentyl)methylcarbamate (217 mg) were dissolved in dimethylformamide (10 ml) under nitrogen at room temperature. To the resulting solution was added sodium hydride (60% in oil) (80 mg). The solution was then allowed to stir at room temperature under nitrogen for 24 h. The mixture was then poured into water and extracted with diethyl ether three times. The combined organic fractions were washed with brine and then dried (MgSO4). The solvent was evaporated and the residue was purified by chromatography (silica, 25% ethyl acetate/isohexane as eluent) to give 175 mg (45%) of the subtitle compound as an oil.

Workup

  1. extractionextracted with diethyl ether three times
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated
  5. customthe residue was purified by chromatography (silica, 25% ethyl acetate/isohexane as eluent)

Sources & evidence

ORD record
ord-eebec1b4cd944bf2b5927b0558a81d41
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

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