Diethylcarbamoyl chloride → HCID 68827190, compound

HRID 450060Notes

Reaction equation

HRID 450060 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4].[CH2:13]([N:15]([CH2:19][CH3:20])[C:16](Cl)=[O:17])[CH3:14]>C1COCC1>[N+:3]([C:6]1[CH:7]=[C:8]([O:12][C:16](=[O:17])[N:15]([CH2:19][CH3:20])[CH2:13][CH3:14])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 111373-NitrophenolHCID 24758Sodium hydride

Product 1

HCID 68827190HCID 68827190, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To slurry of 50% sodium hydride (340 mg, 14.2 mmol) in anhydrous THF was added 3-nitrophenol (1 g, 7.1 mmol) at 0° C. After 10 min at 0-5° C., diethyl carbamyl chloride (1.5 g, 111.0 mmol) was added and the reaction mixture heated to reflux for 12 hr. The reaction mixture was cooled, ice water added, and filtered. The filtrate was concentrated to give the crude product, which was purified by column chromatography over silica gel, using hexane/ethyl acetate (85:15) as eluent to afford diethyl-carbamic acid-3-nitro-phenyl ester (300 mg, 17%).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 12 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customto give the crude product, which
  7. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-49260957db44442084581de53f13f78d
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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