Water → HCID 91257124, compound

HRID 2183836Notes

Reaction equation

HRID 2183836 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1F.[CH:10]1([CH:13]([OH:25])[CH2:14][CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]1.[H-].[Na+].O>CS(C)=O>[CH:10]1([CH:13]([O:25][C:3]2[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:14][CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:20])[CH3:21])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 136173Benzene, 1,4-dichloro-2-fluoro-HCID 86587541HCID 86587541, compound

Product 1

HCID 91257124HCID 91257124, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,4-Dichloro-2-fluorobenzene (165 mg, 1.00 mmol) and (3-cyclopropyl-3-hydroxypropyl)methylcarbamic acid, 1,1-dimethylethyl ester (230 mg, 1.00 mmol) were dissolved in dimethylsulfoxide (10 ml) under nitrogen at room temperature. To the resulting solution was added sodium hydride (60% in oil) (80 mg, 2.00 mmol). 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 dried over magnesium sulfate. The solvent was evaporated and the residue eluted down a flash chromatography column using 10% ethyl acetate/isohexane as eluent to give 175 mg (47%) of the title 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 over magnesium sulfate
  4. customThe solvent was evaporated
  5. washthe residue eluted down a flash chromatography column

Sources & evidence

ORD record
ord-af7727948fac48d39d26021bc64ec562
Source dataset
uspto-grants-2005_05
Patent number
US06900243B2

Reaction notes

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