Diethylcarbamoyl chloride → HCID 11053383, compound

HRID 1627925Notes

Reaction equation

HRID 1627925 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:11]([N:13]([CH2:17][CH3:18])[C:14](Cl)=[O:15])[CH3:12]>O1CCCC1>[CH2:11]([N:13]([CH2:17][CH3:18])[C:14](=[O:15])[O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 79333-ChlorophenolHCID 24758Sodium hydride

Product 1

HCID 11053383HCID 11053383, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chlorophenol (10 g; 78 mmol) in dry tetrahydrofuran (78 ml) under a nitrogen atmosphere was added sodium hydride (60% in oil) (6.22 g; 156 mmol) in small portions. The reaction was stirred at room temperature for 1 h and diethylcarbamic chloride (19.71 ml; 156 mmol) was slowly added and the reaction was stirred at room temperature for 21 h. The reaction was quenched with water, concentrated under reduced pressure, extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (0-40%) in heptane furnished 9.86 g (56%) of 3-chlorophenyl diethylcarbamate.

Workup

  1. stirringthe reaction was stirred at room temperature for 21 h
  2. customThe reaction was quenched with water
  3. concentrationconcentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (0-40%) in heptane

Sources & evidence

ORD record
ord-c4bb9c5dc7ae44ab94586175bb783306
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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